Ethyl trifluoroacetate → HCID 22316660, compound

HRID 396860Notes

Reaction equation

HRID 396860 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-320f7f37e27f4eb8a551100ecf686c1c
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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