Methanol → HCID 68884253, compound

Participants

Reaction Steps

To a mixture of potassium t-butoxide (0.38 g) and dimethoxyethane (10 mL) was added a solution of toluenesulfonylmethylisocyanide (0.33 g) in dimethoxyethane (5 mL) at −78° C. and the mixture was stirred for 10 min. A solution (10 mL) of 3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]benzaldehyde (0.70 g) in dimethoxyethane was added to the reaction mixture and the mixture was stirred for 30 min at −78° C. Methanol (25 mL) was added to the reaction mixture at room temperature and the mixture was heated under reflux for 1 hr. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 2-[3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]phenyl]acetonitrile as an oil (0.295 g, yield 41%) from a fraction eluted with acetone-hexane (1:5, v/v).

Provenance & Evidence