Triphenylphosphine → Methyl 2-[2-[4-[(2-phenyl-5-propyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate

Participants

Reaction Steps

To a mixture of [4-[(2-phenyl-5-propyl-4-oxazolyl)methoxy]phenyl]methanol (0.50 g), methyl 2-(2-hydroxyphenyl)acetate (0.30 g), triphenylphosphine (0.60 g) and tetrahydrofuran (30 mL) was dropwise added a solution (40%, 1.00 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, and 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-phenyl-5-propyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate as an oil (0.40 g, 56%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Provenance & Evidence