Diisobutylaluminum hydride → HCID 14022228, compound

Temperature

0 °C

To a stirred solution of 6-cyclobutylidene-hexanoic acid methyl ester (0.60 g, 3.3 mmol) in toluene (30 mL) was added DIBAL-H (8.2 mL, 1 M solution in hexane, 8.2 mmol) dropwise at 0° C. under N2. After stirring at 0° C. for 30 min, the reaction was quenched by MeOH (3 mL). Saturated aqueous sodium potassium tartrate (20 mL) was added to the reaction mixture. After stirrng 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-cyclobutylidene-hexan-1-ol as a colorless oil, which was used in the next step without further purification.

1. customthe reaction was quenched by MeOH (3 mL)
2. additionSaturated aqueous sodium potassium tartrate (20 mL) was added to the reaction mixture
3. waitAfter stirrng 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-632b3aefbc274b3face44a650ef151e3

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091357B2