Diisobutylaluminum hydride → 6-Cyclohexylidene-hexan-1-ol

온도

0 °C

To a stired solution of 6-cyclohexylidene-hexanoic acid methyl ester (1.28 g, 6.10 mmol) in toluene (60 mL) was added DIBAL-H (15.3 mL, 1 M solution in hexane, 15.3 mmol) dropwise at 0° C. under N2. After stirring at 0° C. for 30 min, the reaction was quenched by MeOH (5 mL). Saturated aqueous sodium potassium tartrate (40 mL) was added to the reaction mixture. After string 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-cyclohexylidene-hexan-1-ol (1.12 g, 100%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.05 (1H, m), 3.62 (2H, t, J=6.6 Hz), 2.05 (6H, m), 1.42–1.64 (8H, m), 1.34 (2H, m); 13C NMR (75 MHz, CDCl3) δ 139.78, 121.25, 63.22, 37.43, 32.96, 30.22, 28.96, 28.11, 27.23, 25.58.

1. customthe reaction was quenched by MeOH (5 mL)
2. additionSaturated aqueous sodium potassium tartrate (40 mL) was added to the reaction mixture
3. waitAfter string 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 기록

ord-e9218e557d5c420fa426c304c9a5e1f0

출처 데이터셋

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07091357B2