Ammonium Chloride → HCID 117759619, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a solution (1.8 M, 5.29 mL) of trimethylaluminum in toluene was added to a solution of 3-(3-(3-((methoxymethoxy)methyl)phenyl)oxiran-2-yl)propanenitrile (1.07 g) in THF (50 mL) at −78° C., and the mixture was stirred at −78° C. for 20 min. To the reaction mixture was added dropwise a solution (1.0 M, 6.49 mL) of lithium hexamethyldisilazane in THF at −78° C., and the mixture was stirred at −78° C. for 30 min. The reaction mixture was stirred at room temperature for 10 min, saturated aqueous ammonium chloride solution was added at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (457 mg, less polar) as a pale-yellow oil and a stereoisomer (345.5 mg, more polar) of the title compound as a pale-yellow oil.

Provenance & Evidence