m-Chloroperbenzoic acid → 3-[2-Methoxy-3-(methylsulfinyl)-4-(trifluoro-methyl)benzoyloxy]cyclohex-2-en-1-one

HRID 215719Notes

Reaction equation

HRID 215719 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[C:29]([S:30][CH3:31])=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=[CH:26][C:15]=1[C:16]([O:18][C:19]1[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[CH:20]=1)=[O:17].S([O-])(O)=O.[Na+]>ClCCl>[CH3:12][O:13][C:14]1[C:29]([S:30]([CH3:31])=[O:9])=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=[CH:26][C:15]=1[C:16]([O:18][C:19]1[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[CH:20]=1)=[O:17]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 669579063-(2-Methoxy-3-methylthio-4-(trifluoromethyl)benzoyloxy)-cyclohex-2-enone

Product 1

HCID 669579183-[2-Methoxy-3-(methylsulfinyl)-4-(trifluoro-methyl)benzoyloxy]cyclohex-2-en-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

68 mg (70% by weight, 0.28 mmol) of meta-chloroperbenzoic acid were added to 100 mg (0.28 mmol) of 3-(2-methoxy-3-methylthio-4-(trifluoromethyl)benzoyloxy)-cyclohex-2-enone in 10 ml of dichloromethane. The mixture was stirred at RT for 1 h. For work-up, 3 ml of 10 percent strength aqueous sodium hydrogensulfite solution were added. After confirmation that no peroxides were present, the organic phase was washed twice with in each case 5 ml of saturated aqueous NaHCO3 solution. After phase separation, the solvent was removed. This gave 90 mg of 3-(2-methoxy-3-methylsulfinyl-4-(trifluoromethyl)benzoyloxy)cyclohex-2-enone.

Workup

  1. washthe organic phase was washed twice with in each case 5 ml of saturated aqueous NaHCO3 solution
  2. customAfter phase separation
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-2aea83e576b046a68fdb4f0fd17ae248
Source dataset
uspto-grants-2012_06
Patent number
US08193121B2

Reaction notes

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