Hydrochloric Acid → 1-Ethoxy-2,2,3,3,3-pentafluoro-1-Propanol

Temperature

-60 °C

Ethyl 2,2,3,3,3-pentafluoropropionate (10.99 grams, 57.2 mmol) was dissolved in anhydrous methanol (57 ml) and cooled under argon to −60° C. Sodium borohydride (2.16 grams, 57.2 mmol) was added in four portions. After the addition was complete, stirring was continued for one hour and the temperature was held below −45° C. The mixture was cooled to −60° C. and 1M hydrochloric acid (172 ml) was added dropwise so that the temperature remained below −45° C. The mixture was slowly warmed to room temperature and extracted with diethylether (3×100 ml). The combined organic phases were washed with water (two times), dried over magnesium sulfate, the solvent was removed under reduced pressure. 9.76 g (50.3 mmol, 88%) were obtained and used directly in the next step.

1. additionAfter the addition
2. customwas held below −45° C
3. temperatureThe mixture was cooled to −60° C.
4. customremained below −45° C
5. temperatureThe mixture was slowly warmed to room temperature
6. extractionextracted with diethylether (3×100 ml)
7. washThe combined organic phases were washed with water (two times)
8. dry with materialdried over magnesium sulfate
9. customthe solvent was removed under reduced pressure
10. custom9.76 g (50.3 mmol, 88%) were obtained

ORD record

ord-d958a42572334a8e86bf74fd219a55db

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877934B2