Trifluoroacetic acid → 4-Methyl-3-formyl-pent-3-en-1-oic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 0.956 g of tert.-butyl 4-methyl-3-formyl-pent-3-enoate in 8.7 ml of methylene chloride was added at 0° to 5° C. to a mixture of 15.5 ml of trifluoroacetic acid and 20 ml of methylene chloride and the mixture was stirred at 5° C. for 3 hours. Cyclohexane was added to the mixture which was then evaporated to dryness under reduced pressure. The residue was empasted with isopropyl ether to obtain 0.444 g of 4-methyl-3-formyl-pent-3-en-1-oic acid melting at 102° C. The mother liquors were chromatographed over silica gel and elution with a 1-1-1 benzene-acetone-chloroform mixture yielded 40 mg of 4-methyl-3-formyl-pent-3-en-1-oic acid melting at 102° C.

Provenance & Evidence