Pyridine → 11-Tetradecenyl acetate, (11Z)-

Participants

Reaction Steps

Acetic anhydride (0.17 mL, 1.8 mmol), then pyridine (86 μL, 1.1 mmol), were added sequentially to alcohol 7 (0.19 g, 0.89 mmol) in CH2Cl2 (1.8 mL), and stirred at room temperature for 12 hours. The mixture was diluted with diethyl ether, washed with saturated aqueous NaHCO3, then brine, dried with Na2SO4, and concentrated. Flash chromatography of the residue (SiO2, 5% EtOAc in hexanes) provided 10 (0.19 g, 84% yield, 77% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.29-5.43 (2H, m), 4.05 (2H, t, J=6.8 Hz), 2.04 (7H, m), 1.61 (2H, m), 1.27 (14H, m), 0.95 (3H, m); 13C NMR (CDCl3): δ 171.4, 131.7, 129.4, 64.8, 32.7, 29.9, 29.7 (2C), 29.4 (2C), 28.7, 27.2, 26.1, 21.2, 20.7, 14.6; HRMS (FAB): 255.2324, [C16H30O2+H]+ requires 255.2319.

Provenance & Evidence