3-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde → 1-(3-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

To 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (Preparation 88A, 0.425 g, 1.036 mmol) in THF (5 mL), cooled to −50° C. was added methylmagnesium bromide (3.0M in diethyl ether) (0.380 mL, 1.139 mmol) over a period of 2 min. The contents were allowed to come to room temperature over a period of 30 min. The reaction mixture was re-cooled to −50° C. and 0.15 mL of methylmagnesium bromide was added and the contents allowed to come to room temperature over a period of 10 min. The reaction mixture was quenched by the slow addition of sat. aq ammonium chloride (3 mL) and extracted into EtOAc (2×15 mL). The EtOAc layer was dried over sodium sulfate and concentrated to yield 1-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethanol (0.44 g, 1.032 mmol, 100% yield) as a tan colored solid. LC/MS M+1=427.

Provenance & Evidence