Methanol → HCID 90060171, compound

Temperature

-78 °C

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).

1. temperatureWhile maintaining the temperature at −78° C.
2. stirringthe mixture was stirred at −78° C. for 10 minutes
3. customthe reaction
4. stirringthe mixture was stirred at 0° C. for 1 hour
5. filtrationAfter insoluble material was filtered off
6. washwashed with dichloromethane
7. extractionthe filtrate was extracted with dichloromethane
8. washthe organic layer was washed with water
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationSubsequently, the organic layer was filtered
11. distillationdichloromethane was distilled off

ORD record

ord-3122d055ed354044b8abb95d258dc94d

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266853B2