1-Pentene → 8-Dodecen-1-ol, 1-acetate, (8Z)-

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By cross metathesis of nonenyl acetate: according to the procedure for compound 12, 8-nonenyl acetate (0.76 g, 4.1 mmol) and 1-pentene (4 mL) in THF (4 mL) were reacted with 1 (0.026 g, 1 mol %) to provide 13 (0.60 g, 65% yield, 85% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 4.05 (2H, t, J=6.8 Hz), 2.05 (3H, s), 2.01 (4H, m), 1.62 (2H, m), 1.27-1.41 (10H, m), 0.90 (3H, t, J=7.4 Hz); 13C NMR (CDCl3): δ 171.2, 129.9, 129.8, 64.7, 29.7, 29.3, 29.2 (2C), 28.6, 27.2, 25.9, 22.9, 21.0, 13.8; HRMS (EI): 227.2021, [C14H26O+H]+ requires 227.2011.

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