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

Temperature

0 °C

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.

1. customthe reaction was quenched by MeOH (12 mL)
2. additionSaturated aqueous sodium potassium tartrate (120 mL) was added to the reaction mixture
3. stirringAfter stirring for 1 h
4. customthe organic layer was separated
5. extractionthe aqueous phase was extracted with ether
6. washThe combined organic layers were washed with water and brine
7. customdried
8. customEvaporation of the solvent

ORD record

ord-6d7be9b2d98a4dcd85a633f7f75d4960

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091357B2