Methanol → HCID 90060171, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, methyl 9,9-difluoro-hexadecanoate (No. 6804231; 990 mg, 3.23 mmol) was dissolved in toluene (14 mL), and cooled to −78° C. While maintaining the temperature at −78° C., a dilution of diisobutylaluminum hydride (DIBAlH, 1.5 M solution in toluene, 2.59 mL, 3.88 mmol) with toluene (3.8 mL) was added dropwise, and the mixture was stirred at −78° C. for 2.0 hours. Methanol (0.86 mL) was added to the reaction solution, and the mixture was stirred at −78° C. for 10 minutes to stop the reaction. A saturated Rochelle salt aqueous solution (4.0 mL) and water (12 mL) were further added and the mixture was stirred at 0° C. for 1 hour. After insoluble material was filtered off and washed with dichloromethane, the filtrate was extracted with dichloromethane, the organic layer was washed with water, and dried over anhydrous sodium sulfate. Subsequently, the organic layer was filtered and dichloromethane was distilled off to obtain a crude product of 9,9-difluoro-hexadecanal (No. 6893452).

Provenance & Evidence