Formamide → 4-(4-Benzyloxyphenyl)oxazole

Participants

Reaction Steps

Formamide (1.0ml) was added to 4'-benzyloxy-2-bromoacetophenone (3.0g) and heated at 130° to 135° C. for 1 hour. Water was added to the reaction product, and the mixture was alkalified with aqueous solution of sodium bicarbonate and then extracted with ethyl acetate. The ethyl acetate layer was washed with saturated saline, treated with activated charcoal, dried with anhydrous sodium sulfate and then concentrated. The residue was purified by column chromatography on silica gel [eluting solvent: ethyl acetate-hexane (1:9)] to give 4-(4-benzyloxyphenyl) oxazole (410 mg, 16.6%). The product was further purified by recrystallization from diethyl etherhexane. m.p. 101°-102° C.

Provenance & Evidence