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  4. Synthesis of Tri- and Tetrasubstituted Furans Catalyzed by Trifluoroacetic Acid
 
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Synthesis of Tri- and Tetrasubstituted Furans Catalyzed by Trifluoroacetic Acid

Auteur(s)
Stauffer, Frederic
Neier, Reinhard 
Institut de chimie 
Date de parution
2000
In
Org. Lett.
Vol.
23
No
2
De la page
3535
A la page
3537
Mots-clés
  • Alkylation
  • Cyclization
  • Cyclocondensation reaction
  • Decarboxylation (prepn. of (acetyl)hydroxyfurans and furanalkanoates)
  • furan acetyl hydroxy prepn
  • acetylhydroxyfuran prepn
  • furanalkanoic acid prepn
  • alkylation decarboxylation acetoacetate
  • furanacetic acid prepn
  • furanpropanoic acid prepn
  • acetoacetate alkylation
  • Alkylation

  • Cyclization

  • Cyclocondensation rea...

  • Decarboxylation (prep...

  • furan acetyl hydroxy ...

  • acetylhydroxyfuran pr...

  • furanalkanoic acid pr...

  • alkylation decarboxyl...

  • furanacetic acid prep...

  • furanpropanoic acid p...

  • acetoacetate alkylati...

Résumé
Substituted 2-hydroxy-3-acetylfurans are synthesized by alkylation of tert-Bu acetoacetate with an ?-haloketone followed by treatment of the obtained intermediate with trifluoroacetic acid (TFA). A second alkylation of the intermediate followed by treatment with trifluoroacetic acid provides access to disubstituted 2-methylfurans. For example, alkylation of tert-Bu acetoacetate with Me 5-bromolevulinate gave 2-acetyl-4-oxoheptanedioic acid 1-(1,1-dimethylethyl) 7-Me ester. Treatment of the latter with trifluoroacetic acid gave 4-acetyl-5-hydroxy-2-furanpropanoic acid Me ester. [on SciFinder(R)]
Identifiants
https://libra.unine.ch/handle/123456789/21515
Type de publication
journal article
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