Oleyl Alcohol → (9z,12e)-Tetradecadien-1-ol

Participants

Reaction Steps

According to the procedure for compound 3, oleyl alcohol (1.0 g, 3.7 mmol) and 1,4-trans-hexadiene (4 mL) in THF (4 mL) were reacted with 1 (0.023 g, 1 mol %) to provide 15 0.53 g, 68% yield, 88% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.32-5.49 (4H, m), 3.64 (2H, br t, J=6.6 Hz), 2.71 (2H, m), 2.03 (2H, m), 1.03 (3H, m), 1.56 (2H, m), 1.25-1.39 (11H, m); 13C NMR (CDCl3): δ 130.4, 129.6, 127.7, 125.1, 63.1, 32.8, 30.4, 29.6, 29.5, 29.4, 29.2, 27.1, 25.7, 17.9; HRMS (FAB): 209.1906, [C14H26O−H]+ requires 209.1905.

Provenance & Evidence