Water → HCID 18385921, compound

HRID 2298330Notes

Reaction equation

HRID 2298330 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12](=[O:17])[C:11]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[CH:6][C:7]=1SC.[CH2:24]1COCC1.O.O[O:31][S:32]([O-:34])=O.[K+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12](=[O:17])[C:11]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[CH:6][C:7]=1[S:32]([CH3:24])(=[O:34])=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 18385719HCID 18385719, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18385921HCID 18385921, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

350 mg of 5-{3-bromo-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 336), dissolved in 50 ml methanol, 50 ml THF and 50 ml water, was reacted with 1.5 g of OXONE by stirring at room temperature for 15 hours. 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 was purified by column chromatography (hexane/ethylacetate=3:2) to yield 173 mg of 5-{3-bromo-4-(methylsulfonyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone as a solid. mp: 154-155° C. NMR: δ1.58 (s, 6H), 3.29 (s, 3H), 7.26 (m, 3H), 7.38 (m, 2H), 8.07 (d, J=1.8 Hz, 1H), 8.10 (d, J=8.1 Hz, 2H). IR (cm−1): 1698, 1585, 1318, 1150.

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/ethylacetate=3:2)

Sources & evidence

ORD record
ord-db44a3e4bd614f148fce342dab3fb98a
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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