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According to the procedure for compound 3, 11-eicosenol (1.3 g, 4.4 mmol) and 1-hexene (6 mL) in THF (6 mL) were reacted with 1 (0.028 g, 1 mol %) to provide 5 (0.84 g, 76% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 3.64 (2H, td, J=6.5, 5.3 Hz), 2.02 (4H, m), 1.56 (2H, m), 1.23-1.38 (19H, m), 0.90 (3H, t, J=7.2 Hz); 13C NMR (CDCl3): δ 129.9 (2C), 63.1, 32.8, 32.0, 29.8, 29.6 (2C), 29.5, 29.4, 29.3, 27.2, 26.9, 25.8, 22.4, 14.0; HRMS (FAB): 241.2536, [C16H32O+H]+ requires 241.2531.

1. customwere reacted with 1 (0.028 g, 1 mol %)
2. customto provide 5 (0.84 g, 76% yield, 86% Z as determined by 1H-NMR) as a colorless oil