Ethyl 3,3,3-trifluoro-2-oxopropanoate → HCID 58333148, compound

To a solution of ethyl 3,3,3-trifluoropyruvate (14.2 g) in THF (200 mL) at −78° C. was added vinyl magnesium bromide (84 mL of 1M in THF) dropwise via addition funnel. The resulting mixture was then warmed to ambient temperature over 2 h. The reaction was quenched by pouring the mixture over ice. To the resulting mixture was then added 2 N HCl, the mixture was extracted with EtOAc, and dried over Na2SO4. After concentration, the resulting crude material was filtered through a plug of silica gel and rinsed with 50% Et2O/hexanes. The resulting mixture was concentrated to yield the title compound as a golden oil.

1. additiondropwise via addition funnel
2. customThe reaction was quenched
3. additionby pouring the mixture over ice
4. additionTo the resulting mixture was then added 2 N HCl
5. extractionthe mixture was extracted with EtOAc
6. dry with materialdried over Na2SO4
7. concentrationAfter concentration
8. filtrationthe resulting crude material was filtered through a plug of silica gel
9. washrinsed with 50% Et2O/hexanes
10. concentrationThe resulting mixture was concentrated

ORD record

ord-1a0dbd13b9984cfdbbad8a8ac9802a01

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802865B2