Ethyl trifluoroacetate → HCID 59210413, compound

HRID 2243265Notes

Reaction equation

HRID 2243265 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[H-].[Na+].[F:16][C:17]([F:24])([F:23])[C:18](OCC)=[O:19]>C1COCC1>[F:16][C:17]([F:24])([F:23])[C:18](=[O:19])[CH2:12][C:11]([C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=1)=[O:13]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydrideHCID 3745834HCID 3745834, compound

Product 1

HCID 59210413HCID 59210413, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF suspension of 1-(3-methyl-4-nitro-phenyl)-ethanone (2.0 g), sodium hydride (0.6 g) was slowly added and the mixture was stirred for 1 hour. After adding ethyl trifluoroacetate (1.6 g), the reaction mixture was refluxed for 5 hours. After cooling, the solvent was distilled off under reduced pressure. The residue was suspended in ethyl acetate and washed with 1N aqueous solution of hydrochloric acid. After drying the organic layer with sodium sulfate, the solvent was distilled off and the obtained residue was purified by silica gel column chromatography to obtain 4,4,4-trifluoro-1-(3-methyl-4-nitro-phenyl)-butane-1,3-dione (2.5 g).

Workup

  1. additionwas slowly added
  2. temperaturethe reaction mixture was refluxed for 5 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off under reduced pressure
  5. washwashed with 1N aqueous solution of hydrochloric acid
  6. dry with materialAfter drying the organic layer with sodium sulfate
  7. distillationthe solvent was distilled off
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5483bf96bb514d2797054b9012619447
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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