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Ethyl trifluoroacetate → Butane-1,3-dione, 4,4,4-trifluoro-1-(4-imidazol-1-ylphenyl)-

HRID 396737
Notes
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Reaction equation

HRID 396737 reaction equation
C[Si](C)(C)N[Si](C)(C)C.C([Li])CCC.[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH:28]=[N:27][CH:26]=[CH:25]2)=[CH:20][CH:19]=1)=[O:17].[F:29][C:30]([F:37])([F:36])[C:31](OCC)=[O:32]>C1COCC1>[F:29][C:30]([F:37])([F:36])[C:31](=[O:32])[CH2:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH:25]=[CH:26][N:27]=[CH:28]2)=[CH:22][CH:23]=1)=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 9794Ethyl trifluoroacetateHCID 13838HexamethyldisilazaneHCID 823161-(4-(1H-Imidazol-1-yl)phenyl)ethanoneHCID 178418339Butyllithium

Product 1

HCID 6426099Butane-1,3-dione, 4,4,4-trifluoro-1-(4-imidazol-1-ylphenyl)-

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-78 °C

Procedure

To a THF (5 mL) solution of 1,1,1,3,3,3-hexamethyldisilazane (0.178 g, 1.1 mmol) was added n-butyl lithum (1.6 M solution in hexane, 0.72 mL, 1.2mmol) at 0° C. under nitrogen, and the mixture was stirred for 30 minutes, and cooled to −78° C. 4-(1-Imidazolyl)acetophenone (prepared according the method of M. A. Khan et, al., J. Chem. Soc. C., 1970, 85., 0.186 g, 1.0 mmol) was added to the mixture, and residue was stirred for 1 hour. Ethyl trifluoroacetate (0.17 g, 1.2 mmol) was added tothe reaction mixture, the residure was warm to room temperature. The reaction mixture was poured into ice water and the whole was extracted with ethyl acetate (30 mL×2). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The resulting solid was washed with small amount of ethyl acetate to give the title compound (0.163 g).

Workup

  1. addition, 0.186 g, 1.0 mmol) was added to the mixture, and residue
  2. stirringwas stirred for 1 hour
  3. customtothe reaction mixture
  4. temperaturethe residure was warm to room temperature
  5. extractionthe whole was extracted with ethyl acetate (30 mL×2)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. washThe resulting solid was washed with small amount of ethyl acetate

Sources & evidence

ORD record
ord-014edeebc2ec4087a1b941830e15dd7f
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06608095B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes