Chlorotrimethylsilane → HCID 86640243, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-cyclohexylaniline (5 g, 28.6 mmol) in 75 ml of dry THF at −70 to −75° C. was added slowly by syringe a solution of 17.7 ml of 1.6 M n-butyllithium. When addition was complete, the resulting mixture was stirred at −70 to −75° C. for 0.5 h. To the stirred mixture was then added 3.61 ml (28.5 mmol) of chlorotrimethylsilane at −70 to −75° C. The mixture was then allowed to warm to RT and stirred at RT for 1.75 h. The mixture was then again cooled to −70 to −75° C. after which was slowly added 17.5 ml of 1.6 M n-butyllithium in hexanes. The mixture was allowed to stir at −70 to −75° C. for 0.5 h after which was added 2.45 ml (28.6 mmol) of epibromohydrin. The mixture was allowed to warm to room temperature and stirred for 2 h at room temperature. The mixture was then poured into 250 ml of cold saturated aqueous sodium bicarbonate, extracted with ethyl acetate, washed with brine, dried (sodium sulfate) and concentrated to provide an orange oil which was then purified by chromatography on silica gel, eluting with ethyl acetate/heptane to provide 3.06 g of the title compound.

Provenance & Evidence