Hydrochloric Acid → 2-[[3-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinonitrile

Participants

Reaction Steps

To a mixture of [3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolyl]methanol (2.00 g), 2-chloro-3-cyanopyridine (1.16 g) and N,N-dimethylformamide (60 mL) was gradually added sodium hydride (60%, oil, 335 mg) under ice-cooling. After stirring the reaction mixture at room temperature for 90 min., water was added to the reaction mixture. The mixture was neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (2.61 g, 96%) of 2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinonitrile from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 139-140° C.

Provenance & Evidence