Hydrochloric Acid → 4,4-Difluorocyclohexane-1-carbaldehyde

Temperature

-70 °C

A mixture of 4,4-difluoro-N-methoxy-N-methylcyclohexane-1-carboxamide obtained in Example 2a (1.7 g, 8.21 mmol) and tetrahydrofuran (60 ml) was cooled to −70° C., a 1.0 M diisobutylaluminum hydride/toluene solution (9.85 ml, 9.85 mmol) was added, and the reaction mixture was stirred at −60° C. for 35 minutes. A 1.0 M diisobutylaluminum hydride/toluene solution (5 ml, 5 mmol) was further added at −65° C., and the reaction mixture was stirred at −70° C. for two hours. A 2 N aqueous hydrochloric acid solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was distilled off to give a crude product of the title compound (1.4 g).

1. stirringthe reaction mixture was stirred at −70° C. for two hours
2. extractionwas extracted with ethyl acetate
3. dry with materialThe organic layer was dried over magnesium sulfate
4. distillationthe solvent was distilled off

ORD record

ord-89beb4bb10bd40f98886f4a602fccef7

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476301B2