反应详情

To a stirred solution of 6-cyclopentylidene-hexanoic acid methyl ester (2.77 g, 14.1 mmol) in toluene (130 mL) was added DIBAL-H (35.3 mL, 1 M solution in hexane, 35.3 mmol) dropwise at 0° C. under N2. After sting at 0° C. for 30 min, the reaction was quenched by MeOH (10 mL). Saturated aqueous sodium potassium tartrate (80 mL) was added to the reaction mixture. After stirring for 1 h, the organic layer was separated and the aqueous phase was extracted with ether. The combined organic layers were washed with water and brine and dried. Evaporation of the solvent gave 6-cyclopentylidene-hexan-1-ol (2.47 g, 98%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.24 (1H, m), 3.63 (2H, t, J=6.6 Hz), 2.21 (4H, m), 1.97 (2H, m), 1.50–1.70 (6H, m), 1.34 (2H, m); 13C NMR (75 MHz, CDCl3) δ 143.28, 120.08, 63.22, 33.82, 33.00, 29.81, 29.75, 28.87, 26.72, 26.63, 25.73.

1. customthe reaction was quenched by MeOH (10 mL)
2. additionSaturated aqueous sodium potassium tartrate (80 mL) was added to the reaction mixture
3. customthe organic layer was separated
4. extractionthe aqueous phase was extracted with ether
5. washThe combined organic layers were washed with water and brine
6. customdried
7. customEvaporation of the solvent