Ethyl trifluoroacetate → 2,2,2-Trifluoro-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-one

HRID 1456330Notes

Reaction equation

HRID 1456330 reaction equation
C([Li])CCC.[CH3:6][C:7]1[N:8]=[CH:9][S:10][CH:11]=1.[F:12][C:13]([F:20])([F:19])[C:14](OCC)=[O:15].[Cl-].[NH4+]>O1CCCC1>[CH3:6][C:7]1[N:8]=[C:9]([C:14](=[O:15])[C:13]([F:20])([F:19])[F:12])[S:10][CH:11]=1

Participants

6

Reactant 4

HCID 9794Ethyl trifluoroacetateHCID 127484-MethylthiazoleHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 221066902,2,2-Trifluoro-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (2.5M solution in hexanes, 40.4 ml) was added dropwise to a stirred solution of 4-methylthiazole (l10 g) in anhydrous tetrahydrofuran at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, ethyl trifluoroacetate (12 ml) was added dropwise. After a further 2 hours the mixture was allowed to warm to room temperature and was, then left stirring overnight. Saturated aqueous ammonium chloride solution was added and the organic phase was separated, dried and evaporated to dryness. The residue was purified by flash chromatography to give the hydrate corresponding to the title compound as a white solid. M.p. 77°-81° C. 13C Nmr (d6 -DMSO) 16.4, 91.1 (q J 32 Hz), 116.3, 122.2 (q, J 287 Hz), 152.0 and 166.6 ppm.

Workup

  1. waitAfter a further 2 hours the mixture was allowed
  2. waitleft
  3. customthe organic phase was separated
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-15fdd352d5e04da084397ec300310c60
Source dataset
uspto-grants-1998_12
Patent number
US05843971

Reaction notes

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