Water → 2-ethyl-2-methyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

HRID 2298289Notes

Reaction equation

HRID 2298289 reaction equation
[CH2:1]([C:3]1([CH3:17])[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12](SC)=[CH:11][CH:10]=2)[O:4]1)[CH3:2].[CH2:18]1COCC1.O.O[O:25][S:26]([O-:28])=O.[K+]>C(O)C>[CH2:1]([C:3]1([CH3:17])[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([S:26]([CH3:18])(=[O:28])=[O:25])=[CH:11][CH:10]=2)[O:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 183860632-ethyl-2-methyl-5-{4-(methylthio)phenyl}-3(2H)-furanoneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 183855812-ethyl-2-methyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude product 2-ethyl-2-methyl-5-{4-(methylthio)phenyl}-3(2H)-furanone from the previous Step 3 was dissolved in 50 ml ethanol, 50 ml THF and 50 ml water, and 10 g of OXONE was added thereto. The reaction mixture was stirred overnight at room temperature. Then the insoluble materials were removed by filtration and the filtrate was concentrated in vacuo. The resulting aqueous layer was extracted with dichloromethane (100 ml×1 and 50 ml×2). The organic layer was concentrated under reduced pressure and the resulting residue was purified by column chromatography (hexane/ethylacetate=2:1) to yield 4.5 g of 2-ethyl-2-methyl-5-{4-(methylsufonyl)phenyl}-3(2H)-furanone. NMR: δ0.89 (t, J=7.2 Hz, 3H), 1.48 (s, 3H), 1.91 (q, J=7.2 Hz, 2H), 3.11 (s, 3H), 6.13 (s, 1H), 8.07 (m, 4H).

Workup

  1. customThen the insoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. extractionThe resulting aqueous layer was extracted with dichloromethane (100 ml×1 and 50 ml×2)
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resulting residue was purified by column chromatography (hexane/ethylacetate=2:1)

Sources & evidence

ORD record
ord-47ae621101b443629c79ff0558628c65
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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