Reaction #302901

ord-2aea83e576b046a68fdb4f0fd17ae248

Reaction equation

O=C(OO)c1cccc(Cl)c1
meta-chloroperbenzoic acid
COc1c(C(=O)OC2=CC(=O)CCC2)ccc(C(F)(F)F)c1SC
3-(2-methoxy-3-methylthio-4-(trifluoromethyl)benzoyloxy)-cyclohex-2-enone
O=S([O-])O.[Na+]
sodium hydrogensulfite
COc1c(C(=O)OC2=CC(=O)CCC2)ccc(C(F)(F)F)c1S(C)=O
3-(2-methoxy-3-methylsulfinyl-4-(trifluoromethyl)benzoyloxy)-cyclohex-2-enone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Washthe organic phase was washed twice with in each case 5 ml of saturated aqueous NaHCO3 solution
  2. 2
    OtherAfter phase separation
  3. 3
    Otherthe solvent was removed

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08193121B2uspto-grants-2012_06