Triethylamine → 2-[2-[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile

Participants

Reaction Steps

To a mixture of [2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanol (1.50 g), triethylamine (0.75 g) and ethyl acetate (150 mL) was dropwise added methanesulfonyl chloride (0.85 g) at room temperature and the mixture was stirred at room temperature for 15 hrs. The reaction mixture was washed successively with water, saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give an oil. A mixture of this oil, sodium cyanide (0.72 g), benzyltributylammonium chloride (0.59 g), acetonitrile (20 mL) and water (10 ml) was stirred at room temperature for 15 hrs. The reaction mixture was concentrated, and ethyl acetate was added to the residue. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (0.55 g, 36%) of 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 149-150° C.

Provenance & Evidence