Dimethyl Sulfoxide → 11-Hexadecenal, (11Z)-

Participants

Reaction Steps

DMSO (0.11 mL, 1.6 mmol) was added dropwise to a solution of oxalyl chloride (0.080 mL, 0.96 mmol) in CH2Cl2 (5 mL) at −78° C., and after 5 minutes a solution of alcohol 5 (0.21 g, 0.87 mmol) in CH2Cl2 (0.9 mL) was added. After stirring for 15 minutes at the same temperature, triethylamine (0.61 mL, 4.4 mmol) was added. The mixture was warmed to room temperature, diluted with Et2O, washed sequentially with 1M HCl, saturated aqueous NaHCO3, brine, dried with Na2SO4, and the solvent was removed in vacuo. Flash chromatography of the residue (SiO2, 10% EtOAc in hexanes) provided 6 (0.20 g, 95% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 9.76 (1H, t, J=1.9 Hz), 5.36 (2H, m), 2.42 (2H, td, J=7.4, 1.9 Hz), 2.02 (4H, m), 1.63 (2H, m), 1.24-1.36 (16H, m), 0.90 (3H, t, J=7.2 Hz); 13C NMR (CDCl3): δ 202.9, 129.9, 129.8, 43.9, 32.0, 29.8, 29.5, 29.4 (2C), 29.3, 29.2, 27.2, 26.9, 22.4, 22.1, 14.0; HRMS (FAB): 237.2209, [C16H30O−H]+ requires 237.2218.

Provenance & Evidence