Diethyl Oxalate → 5,5,5-Trifluoro-2-oxopentanoic acid

Ethyl 4,4,4-trifluorobutyrate (1 g, 5.88 mmol) and diethyl oxalate (3.87 g, 26.5 mmol) was dissolved in ethanol. Sodium ethoxide (21% in ethanol, 2.09 g) was added to the solution, and the reaction mixture stirred for 0.5 hrs. Solvent was distilled, and the residue extracted with EtOAc/water. The organic layers were collected and dried over sodium sulfate. After filtration, solvent was removed to give a clear liquid. MS (ESI): m/z 269.1 (M−1). The liquid was then dissolved in 3N HCl (20 mL), and the reaction mixture refluxed for 4 hrs. After cooling down, the reaction mixture was extracted with EtOAc. The organic layers were collected and dried over sodium sulfate. After filtration, solvent was removed, and the residue used directly in the next step. MS (ESI): m/z 169.7 (M−1).

1. distillationSolvent was distilled
2. extractionthe residue extracted with EtOAc/water
3. customThe organic layers were collected
4. dry with materialdried over sodium sulfate
5. filtrationAfter filtration, solvent
6. customwas removed
7. customto give a clear liquid
8. temperaturethe reaction mixture refluxed for 4 hrs
9. temperatureAfter cooling down
10. extractionthe reaction mixture was extracted with EtOAc
11. customThe organic layers were collected
12. dry with materialdried over sodium sulfate
13. filtrationAfter filtration, solvent
14. customwas removed

ORD record

ord-2358ddc2129b4bbe9e20abdd1871e970

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809529B2