Oleyl Alcohol → 9-Dodecen-1-ol, (9Z)-

Participants

Reaction Steps

In a glovebox, a 25 mL Schlenk flask was charged with oleyl alcohol (1.0 g, 3.7 mmol) and THF (2.5 mL). A solution of 1 (0.047 g, 2 mol %) in THF (0.5 mL) was added and the container was sealed and removed from the glovebox. The flask was attached to a Schlenk line and after three pump/refill cycles, under a positive pressure of argon, the Teflon plug was removed and replaced with a rubber septum. A needle was introduced into the flask and placed into the reaction solution. A slow bubble of 1-butene was introduced and the reaction was allowed to stir with bubbling 1-butene for 4 hours. The reaction was quenched with excess ethyl vinyl ether, and the solvent was removed in vacuo. Flash chromatography of the residue (SiO2, using a slow gradient of hexanes to 9% EtOAc in hexanes) provided 7 (0.27 g, 40% yield, 77% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.29-5.45 (2H, m), 3.63 (2H, t, J=6.6 Hz), 1.94-2.06 (4H, m), 1.56 (2H, p, J=6.7 Hz), 1.29 (11H, m), 0.95 (3H, m); 13C NMR (CDCl3): δ 131.6, 129.3, 63.1, 32.8, 32.6, 29.8, 29.5, 29.4, 29.2, 29.1, 20.5, 14.4; HRMS (FAB): 184.1830, [C12H24O]+ requires 184.1827.

Provenance & Evidence