Methanol → 5-[2-Fluoro-4-(methylsulfonyl)phenyl]-2,2-dimethyl-4-phenyl-3(2H)-furanone

HRID 2298327Notes

Reaction equation

HRID 2298327 reaction equation
[CH3:1][C:2]1([CH3:23])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][C:15]=2[F:22])[O:3]1.[OH2:24].OOS([O-])=O.[K+].C[OH:32]>>[CH3:1][C:2]1([CH3:23])[C:6](=[O:7])[C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:21])(=[O:32])=[O:24])=[CH:16][C:15]=2[F:22])[O:3]1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 18386058HCID 18386058, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 183856735-[2-Fluoro-4-(methylsulfonyl)phenyl]-2,2-dimethyl-4-phenyl-3(2H)-furanone

Procedure

305 mg of 2,2-dimethyl-5-{2-fluoro-4-(methylthio)phenyl}-4-phenyl-3(2H)-furanone (Example 314) was dissolved in 30 ml methanol, 20 ml TBF and 20 ml water, to which 1.4 g of OXONE was added. The reaction mixture was stirred overnight at room temperature. Then the solvent was removed in vacuo and the resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3). The organic layer was concentrated under reduced pressure and then was purified by column chromatography (hexane/acetate=3:2) to obtain 70 mg of 2,2-dimethyl-5-{2-fluoro-4-(methylsulfonyl)phenyl}-4-phenyl-3(2H)-furanone as a solid. mp: 175-176° C. NMR: δ1.57 (s, 6H), 3.10 (s, 3H), 7.22 (m, 2H), 7.28 (m, 3H), 7.75 (dd, J=8.7, 1.8 Hz, 1H), 7.77 (m, 2H). IR (cm−1): 1702, 1408, 1321, 1147. MS (FAB): 361 (m+1).

Workup

  1. customThen the solvent was removed in vacuo
  2. extractionthe resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customwas purified by column chromatography (hexane/acetate=3:2)

Sources & evidence

ORD record
ord-c5920ae245ac4dc999c07c436df769c0
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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