HCID 18385662, compound → HCID 18385919, compound

HRID 2298324Notes

Reaction equation

HRID 2298324 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](SC)=[C:16](F)[CH:15]=2)[O:3]1.O[O:25][S:26]([O-:28])=O.[K+].CO.[CH2:32]1COCC1.O>>[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][CH:17]=[C:16]([S:26]([CH3:32])(=[O:28])=[O:25])[CH:15]=2)[O:3]1

Participants

4

Reactant 3

HCID 18385662HCID 18385662, compoundHCID 21892291Methanol tetrahydrofuran waterHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18385919HCID 18385919, compound

Procedure

To 2,2-dimethyl-5-{3-fluoro-4-(methylthio)phenyl}-4-phenyl-3((2H)-furanone (1.21 g: Example 264) dissolved in 150 ml 1:1:1 methanol/THF/water, was added 2.77 g of OXONE. The mixture was stirred at room temperature for four hours. Then the volatile solvent was removed in vacuo and the resulting solution was diluted with 50 ml water. The aqueous solution was extracted with dichloromethane (30 ml×3). The organic layer was concentrated under reduced pressure and was purified by column chromatography hexane/ethylacetate=4:1) to afford 520 mg of 2,2-dimethyl-5-{3-(methylsulfonyl)phenyl}-4-phenyl-3(2H)-furanone as a solid. mp: 190-191° C. NMR: δ1.55 (s, 6H), 3.23 (s, 3H), 7.26 (m, 2H), 7.38 (m, 3H), 7.56 (m, 2H), 7.92 (m, 1H). IR (cm−1): 1700, 1427, 1324, 1160, 1147. MS (FAB): 361 (m+1).

Workup

  1. customThen the volatile solvent was removed in vacuo
  2. additionthe resulting solution was diluted with 50 ml water
  3. extractionThe aqueous solution was extracted with dichloromethane (30 ml×3)
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customwas purified by column chromatography hexane/ethylacetate=4:1)

Sources & evidence

ORD record
ord-492389a796c84ec59338626dcb5e0e51
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

Loading…