Hydrochloric Acid → Ethyl 4,4,5,5-tetrafluoro-3-hydroxy-pentanoate

Temperature

0 °C

Ethyl 4,4,5,5-tetrafluoro-3-oxo-pentanoate (25.7 g, 0.119 mmol) was dissolved in toluene (260 ml) and cooled to 0° C. Sodium borohydride (5.4 g, 0.143 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 1 m 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 22.9 g of a residue (0.105 mol, 88%) 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-76f5c52579a347a580377e478a065673

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08883791B2