Triethylamine → HCID 68885068, compound

Participants

Reaction Steps

To a mixture of [3-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-2-pyridyl]methanol (0.74 g), triethylamine (0.36 g) and ethyl acetate (50 mL) was dropwise added methanesulfonyl chloride (0.41 g) at room temperature and the mixture was stirred at room temperature for 14 hrs. The reaction mixture was washed successively with water saturated aqueous sodium hydrogencarbonate, 1N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give a yellow oil. To a mixture of this yellow oil and dimethyl sulfoxide (20 mL) was added an aqueous solution (2 mL) of sodium cyanide (0.18 g) at room temperature and the mixture was stirred at room temperature for 2 days. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (0.60 g, 81%) of 2-[3-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-2-pyridyl]acetonitrile from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave pale-brown prism crystals. melting point: 138-139° C.

Provenance & Evidence