Hydrochloric Acid → 4,4,4-Trifluoro-1-(1-cyclohexenyl)-1,3-butanedione

HRID 1860588Notes

Reaction equation

HRID 1860588 reaction equation
[C:1]1([CH2:7][C:8](CC2CCCCC=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[F:17][C:18]([F:25])([F:24])[C:19]([O:21]CC)=O.C[O-:27].[Na+].Cl>COCCOC.O.CCOC(C)=O>[F:25][C:18]([F:17])([F:24])[C:19](=[O:21])[CH2:8][C:7]([C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1)=[O:27]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 10942334Sodium MethoxideHCID 696885601-Cyclohexenylmethylketone

Product 1

HCID 186240894,4,4-Trifluoro-1-(1-cyclohexenyl)-1,3-butanedione

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-cyclohexenylmethylketone (1 ml, 7.8 mmol) in DME (60 ml) was added ethyl trifluoroacetate (2.8 ml, 23.4 mmol) and sodium methoxide (2.2 g, 39 mmol), and the resulting reaction mixture was stirred at room temperature overnight. EtOAc (200 ml) and water (50 ml) were added, and the pH of the aqueous layer was adjusted to 6 by addition of 2 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-d8fd76cb92cc47d38969a30e54f11137
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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