Cyclohexene, 4,4-difluoro-1-[(trimethylsilyl)oxy]- → 4,4-Difluorocyclohex-2-en-1-one

HRID 337855Notes

Reaction equation

HRID 337855 reaction equation
[F:1][C:2]1([F:13])[CH2:7][CH2:6][C:5]([O:8][Si](C)(C)C)=[CH:4][CH2:3]1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1([F:13])[CH2:7][CH2:6][C:5](=[O:8])[CH:4]=[CH:3]1

Participants

4

Reactant 1

HCID 89962723Cyclohexene, 4,4-difluoro-1-[(trimethylsilyl)oxy]-

Product 1

HCID 899621164,4-Difluorocyclohex-2-en-1-oneYield 50.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of the [(4,4-difluorocyclohex-1-en-1-yl)oxy](trimethyl)silane (3.1 g, 15.0 mmol) prepared in Example 88a in acetonitrile (25 mL), palladium acetate (4.0 g, 17.8 mmol) was added, and the mixture was stirred at room temperature for 45 minutes. The reaction solution was filtered, the filtrate was vacuum concentrated, and the residue was purified with silica gel chromatography (hexane/ethyl acetate=9:1) to yield the title compound (1.0 g, 50%) as a yellow oil.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated
  3. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-98f4e68716674df2b71a84d4f7468771
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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