Ammonium Chloride → HCID 69216303, compound

Participants

Reaction Steps

To a mixture of potassium tert-butoxide (700 mg) and dimethoxyethane (10 mL) was added a solution of p-toluenesulfonylmethylisocyanide (650 mg) in dimethoxyethane (10 mL) at −78° C., and the mixture was stirred for 5 min. To the reaction mixture was added a solution of 3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-phenyl-1H-pyrazole-4-carbaldehyde (1.46 g) in dimethoxyethane (10 mL). After stirring at the same temperature for 1 hr, the mixture was stirred for 1 hr while warming to room temperature. To the reaction mixture was added methanol (20 mL), and the mixture was refluxed for 1 hr. After cooling, the reaction mixture was poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give (3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-phenyl-1H-pyrazol-4-yl)acetonitrile (700 mg, yield 47%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:2, v/v). The crystals were recrystallized from ethyl acetate-hexane. melting point: 137-138° C.

Provenance & Evidence