Dimethylformamide → ethyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 3-(2-thienyl)-1H-pyrazole-4-caboxylate (10.23 g), 4-(4-chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole (14.66 g), potassium carbonate (13.09 g), and N,N-dimethylformamide (100 ml) was stirred at 80° C. for 8 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carboxylate as colorless crystals (19.88 g, yield: 87%) from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 113˜114° C.

Provenance & Evidence