Tetrahydrofuran → 6Z-Heneicosen-11-ol
Reaction equation
[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11]C.[CH2:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH2:21]1[CH2:25]OC[CH2:22]1>>[CH3:14][CH2:15][CH2:16][CH2:17][CH2:18]/[CH:19]=[CH:20]\[CH2:22][CH2:21][CH2:25][CH:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]Participants
4
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.