Synthesis of Tri- and Tetrasubstituted Furans Catalyzed by Trifluoroacetic Acid
Author(s)
Stauffer, Frederic
Date issued
2000
In
Org. Lett.
Vol
23
No
2
From page
3535
To page
3537
Subjects
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
Abstract
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)]
Publication type
journal article