Reaction #966227

Reaction equation

THF

compound 12

(Z)-Dodec-8-en-1-ol

1-heptene

→

19

Yield 70.0%

(Z)-Henicos-6-en-11-ol

Yield 70.0%

Conditions

Workup

1. 1
   Otherwere reacted with 1 (0.015 g, 0.5 mol %)

Procedure

According to the procedure for compound 12, compound 18 (1.0 g, 4.2 mmol) and 1-heptene (4 mL) in THF (4 mL) were reacted with 1 (0.015 g, 0.5 mol %) to provide 19 (0.91 g, 70% yield, 88% Z as determined by quantitative 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 3.59 (1H, m), 2.03 (4H, m), 1.21-1.54 (29H, m), 0.88 (6H, m); 13C NMR (CDCl3): δ 130.4, 129.4, 71.9, 37.6, 37.1, 31.9, 31.6, 29.7 (2C), 29.6 (2C), 29.4 (2C), 27.2 (2C), 25.8, 25.7, 22.7, 22.6, 14.1 (2C); HRMS (FAB): 309.3162, [C21H42O−H]+ requires 309.3157.

Source