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data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Benary_reaction" title="Benary reaction">Benary reaction</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1049416944">.mw-parser-output .ib-reactionbox{border-collapse:collapse}.mw-parser-output .ib-reactionbox td,.mw-parser-output .ib-reactionbox th{border:1px solid #a2a9b1}</style> <table class="infobox ib-reactionbox"> <tbody><tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Feist–Benary synthesis </th></tr> <tr> <td>Named after </td> <td>Franz Feist <br /> Erich Benary </td></tr> <tr> <td>Reaction type </td> <td><a href="/wiki/Ring_forming_reaction" title="Ring forming reaction">Ring forming reaction</a> </td></tr> <tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Identifiers </th></tr> <tr> <td><a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">RSC</a> ontology ID </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/ols/ontologies/rxno/terms?iri=http%3A%2F%2Fpurl.obolibrary.org%2Fobo%2FRXNO_0000501">RXNO:0000501</a></span> </td></tr> <tr> <td style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2"> </td></tr> </tbody></table> <p>The <b>Feist–Benary synthesis</b> is an <a href="/wiki/Organic_reaction" title="Organic reaction">organic reaction</a> between <a href="/wiki/%CE%91-Halo_ketone" title="Α-Halo ketone">α-halo ketones</a> and β-<a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">dicarbonyl</a> compounds to produce substituted <a href="/wiki/Furan" title="Furan">furan</a> compounds.<sup id="cite_ref-Gil_1-0" class="reference"><a href="#cite_note-Gil-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> This <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation reaction</a> is <a href="/wiki/Catalysis" title="Catalysis">catalyzed</a> by <a href="/wiki/Amine" title="Amine">amines</a> such as <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> and <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>. The first step in the ring synthesis is related to the <a href="/wiki/Knoevenagel_condensation" title="Knoevenagel condensation">Knoevenagel condensation</a>. In the second step the <a href="/wiki/Enolate" title="Enolate">enolate</a> displaces an <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> <a href="/wiki/Halogen" title="Halogen">halogen</a> in a <a href="/wiki/Nucleophilic_aliphatic_substitution" class="mw-redirect" title="Nucleophilic aliphatic substitution">nucleophilic aliphatic substitution</a>. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:FeistBenarysynthesis.gif" class="mw-file-description" title="Feist Benary synthesis"><img alt="Feist Benary synthesis" src="//upload.wikimedia.org/wikipedia/commons/f/f3/FeistBenarysynthesis.gif" decoding="async" width="478" height="102" class="mw-file-element" data-file-width="478" data-file-height="102" /></a><figcaption>Feist Benary synthesis</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Modifications">Modifications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Feist%E2%80%93Benary_synthesis&action=edit&section=1" title="Edit section: Modifications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In place of α-haloketones, propargyl sulfonium salts can be used to alkylate the diketone.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Another modification is the <a href="/wiki/Enantioselective" class="mw-redirect" title="Enantioselective">enantioselective</a> <b>interrupted Feist-Benary reaction</b><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> with a <a href="/wiki/Chiral_auxiliary" title="Chiral auxiliary">chiral auxiliary</a> based on the <a href="/wiki/Cinchona" title="Cinchona">cinchona</a> <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> <a href="/wiki/Quinine" title="Quinine">quinine</a> based in the presence of <a href="/wiki/Proton_sponge" class="mw-redirect" title="Proton sponge">proton sponge</a> to the hydroxydihydrofuran. This type of alkaloids is also used in asymmetric synthesis in the <a href="/wiki/AD-mix" title="AD-mix">AD-mix</a>. The alkaloid is <a href="/wiki/Protonation" title="Protonation">protonated</a> throughout the reaction and transfers its <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chirality</a> by interaction of the acidic <a href="/wiki/Ammonium_salt" class="mw-redirect" title="Ammonium salt">ammonium</a> hydrogen with the dicarbonyl group of <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">ethyl bromopyruvate</a> in a 5-membered <a href="/wiki/Transition_state" title="Transition state">transition state</a>. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:InterruptedFeistBenary.gif" class="mw-file-description" title="interrupted Feist-Benary reaction"><img alt="interrupted Feist-Benary reaction" src="//upload.wikimedia.org/wikipedia/commons/1/14/InterruptedFeistBenary.gif" decoding="async" width="402" height="287" class="mw-file-element" data-file-width="402" data-file-height="287" /></a><figcaption>interrupted Feist-Benary reaction</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Historic_references">Historic references</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Feist%E2%80%93Benary_synthesis&action=edit&section=2" title="Edit section: Historic references"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFFranz_Feist1902" class="citation journal cs1">Franz Feist (1902). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1426052">"Studien in der Furan- und Pyrrol-Gruppe"</a>. <i><a href="/wiki/Chemische_Berichte" title="Chemische Berichte">Chemische Berichte</a></i>. <b>35</b> (2): 1537–1544. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.19020350263">10.1002/cber.19020350263</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemische+Berichte&rft.atitle=Studien+in+der+Furan-+und+Pyrrol-Gruppe&rft.volume=35&rft.issue=2&rft.pages=1537-1544&rft.date=1902&rft_id=info%3Adoi%2F10.1002%2Fcber.19020350263&rft.au=Franz+Feist&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1426052&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFeist%E2%80%93Benary+synthesis" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFErich_Benary1911" class="citation journal cs1">Erich Benary (1911). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1426435">"Synthese von Pyridin-Derivaten aus Dichlor-äther und β-Amino-crotonsäureester"</a>. <i><a href="/wiki/Chemische_Berichte" title="Chemische Berichte">Chemische Berichte</a></i>. <b>44</b>: 489–493). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.19110440175">10.1002/cber.19110440175</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemische+Berichte&rft.atitle=Synthese+von+Pyridin-Derivaten+aus+Dichlor-%C3%A4ther+und+%CE%B2-Amino-crotons%C3%A4ureester&rft.volume=44&rft.pages=489-493%29&rft.date=1911&rft_id=info%3Adoi%2F10.1002%2Fcber.19110440175&rft.au=Erich+Benary&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1426435&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFeist%E2%80%93Benary+synthesis" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Feist%E2%80%93Benary_synthesis&action=edit&section=3" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-Gil-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Gil_1-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGilchrist1997" class="citation book cs1">Gilchrist, Thomas L. (1997). <i>Heterocyclic Chemistry</i> (3rd ed.). Liverpool: Longman. p. 209-212.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Heterocyclic+Chemistry&rft.place=Liverpool&rft.pages=209-212&rft.edition=3rd&rft.pub=Longman&rft.date=1997&rft.aulast=Gilchrist&rft.aufirst=Thomas+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFeist%E2%80%93Benary+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFP._D._Howes,_C._J._M._Stirling1973" class="citation journal cs1">P. D. Howes, C. J. M. Stirling (1973). "3-Acetyl-2,4-Dimethylfuran". <i>Organic Syntheses</i>. <b>53</b>: 1. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.053.0001">10.15227/orgsyn.053.0001</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=3-Acetyl-2%2C4-Dimethylfuran&rft.volume=53&rft.pages=1&rft.date=1973&rft_id=info%3Adoi%2F10.15227%2Forgsyn.053.0001&rft.au=P.+D.+Howes%2C+C.+J.+M.+Stirling&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFeist%E2%80%93Benary+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCalter,_M._A.Phillips,_R._M.Flaschenriem,_C.2005" class="citation journal cs1">Calter, M. A.; Phillips, R. M.; Flaschenriem, C. (2005). "Catalytic, Asymmetric, "Interrupted" Feist-Bénary Reactions". <i><a href="/wiki/Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">Journal of the American Chemical Society</a></i>. <b>127</b> (42): 14566–14567. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja055752d">10.1021/ja055752d</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16231897">16231897</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Catalytic%2C+Asymmetric%2C+%22Interrupted%22+Feist-B%C3%A9nary+Reactions&rft.volume=127&rft.issue=42&rft.pages=14566-14567&rft.date=2005&rft_id=info%3Adoi%2F10.1021%2Fja055752d&rft_id=info%3Apmid%2F16231897&rft.au=Calter%2C+M.+A.&rft.au=Phillips%2C+R.+M.&rft.au=Flaschenriem%2C+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFeist%E2%80%93Benary+synthesis" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Feist–Benary_synthesis&oldid=1174978724">https://en.wikipedia.org/w/index.php?title=Feist–Benary_synthesis&oldid=1174978724</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Ring_forming_reactions" title="Category:Ring forming reactions">Ring forming reactions</a></li><li><a href="/wiki/Category:Oxygen_heterocycle_forming_reactions" title="Category:Oxygen heterocycle forming reactions">Oxygen heterocycle forming reactions</a></li><li><a href="/wiki/Category:Heterocycle_forming_reactions" title="Category:Heterocycle forming reactions">Heterocycle forming reactions</a></li><li><a href="/wiki/Category:Name_reactions" title="Category:Name reactions">Name reactions</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 11 September 2023, at 23:56<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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