Water → HCID 18385654, compound

HRID 2298338Notes

Reaction equation

HRID 2298338 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:25])[C:11]([CH3:24])([CH3:23])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17](SC)=[C:16]([CH3:22])[CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH2:26]1COCC1.O.O[O:33][S:34]([O-:36])=O.[K+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:25])[C:11]([CH3:24])([CH3:23])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:34]([CH3:26])(=[O:36])=[O:33])=[C:16]([CH3:22])[CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 18385648HCID 18385648, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18385654HCID 18385654, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

105 mg of 4-(3,5-difluorophenyl)-2,2-dimethyl-5-{3-methyl-4-(methylthio)-phenyl}-3(2H)-furanone (Example 381) was dissolved in 50 ml methanol, 30 ml THF and 50 ml water, to which was added 513 mg of OXONE. The reaction mixture was stirred at room temperature for 4 hours. Then the mixture was concentrated in vacuo, and was extracted with water 50 ml and dichloromethane (30 ml×3). Concentration of the organic layer under reduced pressure was followed by column chromatography (hexane/ethylacetate=3:2) to give 97 mg of 4-(3,5-difluorophenyl)-2,2-dimethyl-5-{3-methyl-4-(methylsulfonyl)phenyl}-3(2H)-furanone. NMR: δ1.57 (s, 6H), 2.71 (s, 3H), 3.05 (s, 3H), 6.82 (m, 1H), 7.12 (m, 1H), 7.59 (m, 1H), 7.63 (m, 1H), 7.92 (m, 2H).

Workup

  1. concentrationThen the mixture was concentrated in vacuo
  2. extractionwas extracted with water 50 ml and dichloromethane (30 ml×3)

Sources & evidence

ORD record
ord-da40415d231d4d55974ea5d3018dd2c1
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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