1-Dodecene → 40642-44-2

Participants

Reaction Conditions

Reaction Steps

In a glovebox, a 20 mL vial was charged with 4-pentenol (410 μL, 3.98 mmol), 1-dodecene (4.4 mL), and THF (2.7 mL). A solution of 1 (0.025 g, 1 mol %) in THF (0.5 mL) was added, and the mixture was stirred in an open vial for 6 hours at 35° C. 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 8% EtOAc in hexanes) provided 21 (0.56 g, 62% yield, 84% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.38 (2H, m), 3.65 (2H, m), 1.95-2.14 (4H, m), 1.63 (2H, m), 1.52 (1H, s), 1.25 (16H, m), 0.87 (3H, t, J=6.9 Hz); 13C NMR (100 Hz, CDCl3): δ 131.0, 128.9, 62.8, 32.8, 32.1, 29.9, 29.8, 29.7 (2C), 29.5 (2C), 29.3, 23.7, 22.8, 14.2; HRMS (FAB): 227.2372, [C15H30O+H]+ requires 227.2369.

Provenance & Evidence