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

HRID 1377550Notes

Reaction equation

HRID 1377550 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 (10 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.

Workup

  1. waitAfter a further 2 hours the mixture was allowed
  2. waitwas then left
  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-dc67baae4ea3436781168a0ee74b9e38
Source dataset
uspto-grants-1997_09
Patent number
US05665747

Reaction notes

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