Sodium Hydroxide → HCID 18385668, compound

HRID 2298331Notes

Reaction equation

HRID 2298331 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]=1[S:8][CH3:9].ClC1C=C(C=CC=1)C(OO)=[O:29].[OH-].[Na+]>ClCCl>[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:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:9])=[O:29]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 18385719HCID 18385719, compound

Product 1

HCID 18385668HCID 18385668, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

391 mg of 5-{3-bromo-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 336) dissolved in 50 ml dichloromethane was stirred at 0° C. for 50 minutes in the presence of 183 mg of 70% m-chloroperoxybenzoic acid. Then 10 ml 5% aqueous sodium hydroxide was added to the reaction mixture and the mixed solution was stirred for another 10 minutes. The dichloromethane was removed in vacuo and the resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3). The organic layer was then concentrated under reduced pressure and was purified by column chromatography (hexane/ethylacetate=1:1) to give 310 mg of 5-(3-bromo-4-(methylsulfinyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone. NMR: δ1.58 (s, 6H), 2.84 (s, 3H), 7.30 (m, 2H), 7.38 (m, 3H), 7.78 (dd, J=8.4, 1.8 Hz, 1H), 7.88 (d, J=5.4 Hz, 1H), 7.90 (d, J=2.7 Hz, 1H). IR (cm−1): 1698, 1619, 1388, 1064.

Workup

  1. customThe dichloromethane was removed in vacuo
  2. extractionthe resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3)
  3. concentrationThe organic layer was then concentrated under reduced pressure
  4. customwas purified by column chromatography (hexane/ethylacetate=1:1)

Sources & evidence

ORD record
ord-745ba7cb908344dab3503773498fe35b
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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