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 mol) was dissolved in toluene (260 ml) and cooled to 0° C. Sodium borohydride (5.4 g, 0.143 mol) 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 reduced under reduced pressure. The residue was dissolved in a minimum amount of methanol and evaporated to dryness under reduced pressure to yield 22.9 g (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. dissolutionThe residue was dissolved in a minimum amount of methanol
6. customevaporated to dryness under reduced pressure
7. customto yield 22.9 g (0.105 mol, 88%) that

ORD record

ord-6c11e16691494cbc8fd8f84292e0e77b

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877934B2