Sodium Chloride → HCID 10518344, compound

Participants

Reaction Steps

Diisobutylaluminium hydride (10.7 mL, 60 mmol) dissolved in toluene (30 mL) was precooled to -80° C. and added during 1 h at a temperature of -80° C. to a solution of the crude methyl (S)-3-(2-methoxyprop-2-oxy)tetradecanoate (IX, 13.20 g, 40 mmol) in toluene (100 mL), obtained according to the foregoing described procedure. After complete addition the mixture was stirred for an additional 30 min, diluted with methanol (10 mL), and allowed to warm up to room temperature. A saturated aqueous solution of sodium chloride was added and the precipitate removed by filtration over a pad of fine sand. The filter cake was washed with ethyl acetate (5×15 mL). Filtrate and washings were combined. The aqueous phase was separated and extracted with ethyl acetate (3×20 mL). The combined organic phases were washed with water (10 mL), dried (Na2SO4), and concentrated under reduced pressure. The residual colorless oil (13.7 g, containing still traces of toluene) was used in the next step without further purification. [α]25D +4.89 (c=0.5 in hexane); 1H NMR (DMSO-D6) δ 0.86 (t, J=7 Hz, 3H), 1.24-1.69 (m, 26H), 3.08 (s, 3H), 4.17-4.21 (m, 1H), 9.67 (t, J=2 Hz, 1H), 13C NMR (DMSO-D6) δ 13.85, 22.05, 24.49, 24.87, 24.96, 28.68, 28.94, 28.97, 29.00, 29.04, 31.28, 35.56, 48.50, 48.93, 66.25, 100.48, 202.80. Anal. Calcd for C18H36O4 : C, 71.95; H, 12.08. Found: C, 72.05; H, 12.28.

Provenance & Evidence