Acetonitrile → (3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-methoxybutanenitrile

Participants

Reaction Steps

To a solution of 1.6 M n-butyllithium/hexane solution (20 ml) in THF (50 mL) was added dropwise a solution of acetonitrile (1.23 g) in THF (5 mL) at −78° C., and the mixture was stirred for 15 min, and at −40° C. for 15 min. A solution of 1-(3,4-dichlorophenyl)-2-methoxyethanone (5.00 g) in THF (30 mL) was added dropwise at −78° C., and the mixture was gradually warmed with stirring to room temperature, and stirred for 20 min. The reaction mixture was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-100%)) to give the title compound (5.63 g).

Provenance & Evidence