Triphenylphosphine → Methyl 2-[2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]benzyloxy]phenyl]acetate

Participants

Reaction Steps

To a mixture of [4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]phenyl]methanol (0.60 g), methyl 2-(2-hydroxyphenyl)acetate (0.35 g), triphenylphosphine (0.79 g) and tetrahydrofuran (50 mL) was dropwise added a solution (40%, 1.39 g) of diethyl azodicarboxylate in toluene at room temperature, and the mixture was stirred for 15 hrs. To the reaction mixture was added ethyl acetate, the mixture was washed successively with water, a 2N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 2-[2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]benzyloxy]phenyl]acetate as a colorless oil (0.54 g, 58%) from a fraction eluted with ethyl acetate-hexane (1:6, v/v).

Provenance & Evidence