Potassium Hydroxide → (E)-1-cyclopropyl-1-[4-(difluoromethoxy)phenyl]-N-[(2-methyl-3-phenylphenyl)methoxy]methanimine

Participants

Reaction Steps

Under a dry argon atmosphere a solution of 1.0 g (0.0044 mole) of (E)-(4-difluoromethoxyphenyl)(cyclopropyl)methanone oxime in 50 ml of dry tetrahydrofuran was added to a stirred solution of 0.95 g (0.0044 mole) of 3-chloromethyl-2-methyl [1,1'-biphenyl], 0.29 g (0.0044 mole) of powdered potassium hydroxide, and 0.14 g (0.00044 mole) of tetrabutylammonium bromide in 45 ml of dry tetrahydrofuran. The reaction mixture was stirred at room temperature for approximately 18 hours then evaporated under reduced pressure to give a liquid. The liquid was diluted with methylene chloride, and the mixture washed with water. The aqueous wash was extracted with methylene chloride. The organic phases were combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure to give an oil. The oil was subjected to column chromatography on silica gel, eluting with toluene to give 1.73 g of (E)-(4-difluoromethoxyphenyl)(cyclopropyl)methanone O-[(2-methyl[1,1'-biphenyl]-3-yl)methyl]oxime as an oil.

Provenance & Evidence