Diisobutylaluminum hydride → 7-Methyl-oct-6-en-1-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7-methyl-oct-6-enoic acid methyl ester (3.29 g, 19.4 mmol) in toluene (180 mL) was added DIBAL-H (48.5 mL, 1 M solution in hexane, 48.5 mmol) dropwise at 0° C. under N2. After stirring at 0° C. for 30 min, the reaction was quenched by MeOH (12 mL). Saturated aqueous sodium potassium tartrate (120 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 7-methyl-oct-6-en-1-ol (2.70 g, 98%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.11 (1H, m), 3.63 (2H, m), 1.99 (2H, m), 1.68 (3H, s), 1.59 (3H, s), 1.53 (2H, m), 1.25–1.45 (4H, m); 13C NMR (75 MHz, CDCl3) δ 131.52, 124.69, 63.25, 33.00, 29.95, 28.25, 26.02, 25.69, 17.98.

Provenance & Evidence