Diisobutylaluminum hydride → HCID 14022229, compound

Participants

Reaction Steps

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.

Provenance & Evidence