Methanol → 2,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

HRID 2298269Notes

Reaction equation

HRID 2298269 reaction equation
[CH3:1][C:2]1([CH3:23])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][C:18](SC)=[CH:17][CH:16]=2)[O:3]1.[CH3:24]O.O.O[O:28][S:29]([O-:31])=O.[K+]>C1COCC1>[CH3:1][C:2]1([CH3:23])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([S:29]([CH3:24])(=[O:31])=[O:28])=[CH:17][CH:16]=2)[O:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 183855844-(3-Fluorophenyl)-2,2-dimethyl-5-(4-(methylthio)phenyl)furan-3(2H)-oneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 99507622,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Alternatively, the titled compound was prepared as described in the following procedure: 3.0 g of 2,2-dimethyl-4(3-fluorophenyl)-5-{4-(methylthio)phenyl}-3(2H)-furanone (Example 166) was dissolved in 50 ml THF, 50 ml methanol and 50 ml water along with 10 g of OXONE. The reaction mixture was stirred at room temperature for 2 hours. Then the solution was concentrated in vacuo and the resulting aqueous solution was extracted with 150 ml methylene chloride. The organic layer was washed with brine and then was dried over anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration and the filtrate was concentrated in vacuo. The resulting residue was recrystallized from methylene chloride/hexane to afford 3.3 g of 2,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone.

Workup

  1. customAlternatively, the titled compound was prepared
  2. concentrationThen the solution was concentrated in vacuo
  3. extractionthe resulting aqueous solution was extracted with 150 ml methylene chloride
  4. washThe organic layer was washed with brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customThe magnesium sulfate was removed by filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe resulting residue was recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-3d23c6cf57b648e99d0566fe878d2c14
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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