1-Hexene → Myristoleyl alcohol

Participants

Reaction Steps

In a glovebox, a 20 mL vial was charged with oleyl alcohol (1.0 g, 3.7 mmol), 1-hexene (4 mL), and THF (4 mL). A solution of 1 (0.023 g, 1 mol %) in THF (0.5 mL) was added, and the mixture was stirred in an open vial for 5 hours. The vial was removed from the glovebox, the reaction was quenched with excess ethyl vinyl ether, and the solvent was removed in vacuo. Flash chromatography of the residue (SiO2, using a gradient of hexanes to 20% EtOAc in hexanes) provided 3 (0.73 g, 77% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.35 (2H, m), 3.64 (2H, td, J=6.6, 5.3 Hz), 2.02 (4H, m), 1.57 (2H, m), 1.22-1.39 (15H, m), 0.90 (3H, t, J=7.1 Hz); 13C NMR (CDCl3): δ 129.9, 129.8, 63.1, 32.8, 32.0, 29.8, 29.5, 29.4, 29.2, 27.2, 26.9, 25.7, 22.4, 14.0; HRMS (FAB): 213.2215, [C14H28O+H]+ requires 213.2218.

Provenance & Evidence