HCID 18385936, compound → HCID 18385659, compound

HRID 2298334Notes

Reaction equation

HRID 2298334 reaction equation
[Cl: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.O[O:25][S:26]([O-:28])=O.[K+].CO.[CH2:32]1COCC1.O>>[Cl: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:26]([CH3:32])(=[O:28])=[O:25]

Participants

4

Reactant 3

HCID 18385936HCID 18385936, compoundHCID 21892291Methanol tetrahydrofuran waterHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18385659HCID 18385659, compound

Procedure

1.2 g of 5-{3-chloro-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 354) was dissolved in 150 ml of 1:1:1 methanol/THF/water, to which was added 2.8 g of OXONE. The reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated in vacuo and the resulting residue was extracted with 50 ml water and ethylacetate (100 ml×3). The organic layer was concentrated in vacuo and was purified by column chromatography hexane/ethylacetate=3:1) to give 1.1 g of 5-{3-chloro-4-(methylsulfonyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone as a solid. mp: 174-175° C. NMR: δ1.58 (s, 6H), 3.28 (s, 3H), 7.27 (m, 3H), 7.39 (m, 2H), 7.66 (dd, J=8.4, 1.8 Hz, 1H), 7.86 (d, J=1.8 Hz, 1H), 8.09 (d, J=8.4 Hz, 1H). IR (cm−1): 1700, 1587, 1391, 1321, 1241, 1152.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthe resulting residue was extracted with 50 ml water and ethylacetate (100 ml×3)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customwas purified by column chromatography hexane/ethylacetate=3:1)

Sources & evidence

ORD record
ord-495dd00555744342ba7359b2b9db86fe
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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