Hydrochloric Acid → Ethyl 4,4-difluoro-3-hydroxy-pentanoate

Temperature

0 °C

Ethyl 4,4-difluoro-3-oxo-pentanoate (12.4 g, 0.068 mmol) was dissolved in toluene (100 ml) and cooled to 0° C. Sodium borohydride (3.12 g, 0.083 g) was added portionwise, and the mixture was allowed to reach room temperature overnight with stirring. The mixture was then cooled to 0° C. and acidified with 1M HCl. The phases were separated, the aqueous phase was extracted two times with ethyl acetate, the combined organic phases were dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was dissolved in a minimum amount of methanol, the resulting solution was evaporated to dryness under reduced pressure to yield 8.76 g of a residue (0.048 mol, 70%) that were used directly in the next step.

1. temperatureThe mixture was then cooled to 0° C.
2. customThe phases were separated
3. extractionthe aqueous phase was extracted two times with ethyl acetate
4. dry with materialthe combined organic phases were dried over magnesium sulfate
5. customthe solvent was removed under reduced pressure
6. dissolutionThe residue was dissolved in a minimum amount of methanol
7. customthe resulting solution was evaporated to dryness under reduced pressure

ORD record

ord-5e4f5e877e50421fa518d1b539e42686

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260441B2