Hydrochloric Acid → 1-Cyclohexyl-4,4,4-trifluoro-butane-1,3-dione

HRID 1860578Notes

Reaction equation

HRID 1860578 reaction equation
[CH:1]1([C:7]([CH3:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:10][C:11]([F:18])([F:17])[C:12](OCC)=[O:13].C[O-].[Na+].Cl>COCCOC.O.CCOC(C)=O>[F:10][C:11]([F:18])([F:17])[C:12](=[O:13])[CH2:9][C:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 13207Cyclohexyl methyl ketoneHCID 10942334Sodium Methoxide

Product 1

HCID 110314321-Cyclohexyl-4,4,4-trifluoro-butane-1,3-dione

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of cyclohexylmethylketone (2.75 g, 21.8 mmol) in DME (200 mL) was added ethyl trifluoroacetate (7.79 ml, 65.4 mmol) and sodium methoxide (7.71 g, 131 mmol), and the resulting reaction mixture was stirred at room temperature overnight. EtOAc (500 ml) and water (50 ml) were added, and the pH of the aqueous layer was adjusted to 6 by addition of 1 N HCl solution. The organic layer was washed with brine (50 ml), dried over MgSO4, and concentrated in vacuo to give the title compound in quantitative yield. This was used for the next coupling step without further purification.

Workup

  1. customthe resulting reaction mixture
  2. washThe organic layer was washed with brine (50 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2f0e22902644495b39077ae14c54db2
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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