Ethyl trifluoroacetate → HCID 22316660, compound

HRID 497303Notes

Reaction equation

HRID 497303 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[CH:10][S:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[C:13](=[O:15])[CH3:14].[F:16][C:17]([F:24])([F:23])[C:18](OCC)=[O:19].C[O-].[Na+]>C(OC)(C)(C)C>[F:16][C:17]([F:24])([F:23])[C:18](=[O:19])[CH2:14][C:13]([C:3]1[CH:4]=[CH:5][C:6]([C:8]2[N:9]=[CH:10][S:11][CH:12]=2)=[CH:7][C:2]=1[F:1])=[O:15]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 10942334Sodium MethoxideHCID 223166161-[2-Fluoro-4-(4-thiazolyl)phenyl]ethanone

Product 1

HCID 22316660HCID 22316660, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a stirred solution of 1-[2-fluoro-4-(1,3-thiazol-4-yl)phenyl]-1-ethanone (2.03 g, 9.18 mmol) in t-butylmethylether (60 ml) was added ethyl trifluoroacetate (1.56 g, 11.01 mmol), sodium methoxide (28 wt. % solution in methanol; 2.49 ml, 11.01 mmol) at 0° c., and the mixture was stirred for 3 hours. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give title compound (2.92 g, 99% yield). The compound was used for next reaction without purification.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a37a61a6aa464afbb1d3d0e40a4373a1
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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