Hydrochloric Acid → 3-Nonanol, (3S)-

Participants

Reaction Conditions

Reaction Steps

At room temperature, a three-neck flask equipped with a reflux condenser, internal thermometer, dropping funnel and stirrer under protective nitrogen gas was initially charged with 0.16 g of (1S,2R)-(−)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol (0.6 mmol) in 18 ml of hexane and 1.4 g of nonanal (10 mmol) were added. The mixture was stirred for 15 min and cooled to 0° C. 12 ml of a 1 M solution of diethylzinc in hexane (12 mmol) were added to this mixture, and the mixture was stirred at 0° C. for 14 h. 1.6 g of trimethylchlorosilane (15 mmol) were then added, and the mixture was heated to 40° C. for 30 min. 1.3 g of piperazine (15 mmol) were then added and the mixture was stirred for 60 min. At −10° C., 2.3 ml of 6 N hydrochloric acid were subsequently added and the mixture was stirred at 15° C. for 30 min. After water together with hexane had been distilled off, 40 ml of pentane were added, the suspension was cooled to −20° C. and solid formed was filtered off. The solid was washed three times with 10 ml of cold pentane. Pentane was distilled off under reduced pressure (recovery of pentane) and the desired product (S)-(+)-3-nonanol was obtained in a yield of 1.6 g (89% of theory) and a purity of >95% and 87% ee (HPLC). The zinc content of the product was 30 ppm (ICP).

Provenance & Evidence