Ammonia → HCID 54223055, compound

Participants

Reaction Steps

A solution of a Grignard reagent, prepared from 9.79 g (60.0 mmol) of cyclohexyl bromide and 1.46 g (60.0 mmol) of magnesium, in 85 ml of tetrahydrofuran was added dropwise over a period of 10 minutes to a suspension of 1.90 g (9.98 mmol) of cuprous iodide in 50 ml of tetrahydrofuran at -75° C. The mixture was allowed to stand for 10 minutes, and then a solution of 8.21 g (50.0 mmol) of (S)-benzyloxymethyloxirane, [α]D =+4.82° (c=1, toluene), in 20 ml of tetrahydrofuran was added dropwise over a period of 15 minutes. The resulting mixture was stirred for 3 hours at the same temperature and then for 30 minutes at 0° C. At the end of this time, the reaction was stopped by adding a saturated aqueous solution of ammonium chloride. The reaction mixture was then mixed with 20 ml of concentrated aqueous ammonia, after which it was extracted with diethyl ether. The extract was washed with a saturated aqueous solution of ammonium chloride, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was then dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 250 g of silica gel, using a 1:4 by volume mixture of ethyl acetate and methylene chloride as the eluent, to give 10.0 g (yield 82%) of the title alcohol derivative as a colorless oil.

Provenance & Evidence