Water → Methyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolecarboxylate

Participants

Reaction Steps

To a solution of methyl 3-hydroxyisoxazole-5-carboxylate (5.01 g) in N,N-dimethylformamide (70 mL) was added sodium hydride (60%, oil, 1.40 g) at 0° C. and, after stirring the mixture for 15 min., 4-chloromethyl-5-methyl-2-phenyloxazole (7.26 g) was added. After stirring the mixture at 60° C. for 2 hrs., the reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolecarboxylate (7.96 g, yield 72%) as colorless crystals from a fraction eluted with tetrahydrofuran-hexane (1:1, v/v). The crystals were recrystallized from tetrahydrofuran-hexane. melting point: 123-124° C.

Provenance & Evidence