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Synthesis of Tri- and Tetrasubstituted Furans Catalyzed by Trifluoroacetic Acid
Auteur(s)
Stauffer, Frederic
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
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
Type de publication
journal article
