Dimethylformamide → 4-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(5-methyl-2-thienyl)oxazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[3-(4-hydroxyphenyl)propyl]imidazole (465 mg), 4-chloromethyl-2-(5-methyl-2-thienyl)oxazole (600 mg), potassium carbonate (315 mg) and N,N-dimethylformamide (15 ml) was stirred at 80° C. for 14 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-methanol (20:1, v/v), crystals of 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(5-methyl-2-thienyl)oxazole (490 mg, 56%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 83-84° C.

Provenance & Evidence