1-Pentene → 8-Dodecen-1-ol, (8Z)-

Beteiligte Stoffe

Reaktionsschritte

In a glovebox, a 20 mL vial was charged with 8-nonenol (0.58 g, 4.1 mmol), 1-pentene (4 mL), and THF (4 mL). A solution of 1 (0.026 g, 1 mol %) in THF (0.5 mL) was added, and the mixture was stirred in an open vial for 4 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 12 (0.56 g, 73% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 3.64 (2H, br t, J=5.3 Hz), 2.01 (4H, m), 1.36 (2H, m), 1.28-1.40 (11H, m), 0.90 (3H, t, J=7.4 Hz); 13C NMR (CDCl3): δ 130.0, 129.7, 63.1, 32.8, 29.3 (4C), 27.2, 25.7, 22.9, 13.8; HRMS (EI): 184.1805, [C12H24O]+ requires 184.1827.

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