Methanol → HCID 18385981, compound

HRID 2298301Notes

Reaction equation

HRID 2298301 reaction equation
[CH2:1]([C:3]1([CH2:17][CH3:18])[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].O[O:20][S:21]([O-:23])=O.[K+].[CH3:25]O>O>[CH2:17]([C:3]1([CH2:1][CH3:2])[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([S:21]([CH3:25])(=[O:23])=[O:20])=[CH:11][CH:10]=2)[O:4]1)[CH3:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 18385696HCID 18385696, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18385981HCID 18385981, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of the crude 2,2-diethyl-5-{4-(methylthio)phenyl}-3(2H)-furanone (5.6 g) obtained in the previous step in 50 ml TBF and 50 ml methanol, was added dropwise 20 g of OXONE dissolved in 50 ml water at 0° C. Then the mixture was then stirred at room temperature for 14 hours. The insoluble materials were filtered off and the filtrate was concentrated in vacuo. The resulting residue was extracted with water and ethylacetate (150 ml×2). The ethylacetate layer was concentrated and the resulting crude product was purified by column chromatography (hexane/ethylacetate=2:1) to give 4.5 g of 2,2-diethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone as a solid. mp: 109-110° C. NMR: 0.86 (t, J=7.5 Hz, 6H), 1.91 (q, J=7.5 Hz, 4H), 3.10 (s, 3H), 6.14 (s, 1H), 8.04 (d, J=9.0 Hz, 2H), 8.09 (d, J=9.0 Hz, 2H). IR (cm−1): 2973, 1695, 1588, 1561, 1408, 1315, 1152.

Workup

  1. filtrationThe insoluble materials were filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. extractionThe resulting residue was extracted with water and ethylacetate (150 ml×2)
  4. concentrationThe ethylacetate layer was concentrated
  5. customthe resulting crude product was purified by column chromatography (hexane/ethylacetate=2:1)

Sources & evidence

ORD record
ord-469a851422ea43cfa89256066843c6b4
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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