m-Chloroperbenzoic acid → HCID 18385610, compound

HRID 2298342Notes

Reaction equation

HRID 2298342 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[O:14][C:13]([CH3:16])([CH3:15])[C:12](=[O:17])[C:11]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.ClC1C=C(C=CC=1)C(OO)=[O:29].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:9])=[O:29])[CH:5]=[CH:4][C:3]=1[C:10]1[O:14][C:13]([CH3:16])([CH3:15])[C:12](=[O:17])[C:11]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 18385789HCID 18385789, compound

Product 1

HCID 18385610HCID 18385610, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution 2.7 g of 5-{2-chloro-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 387) in 80 ml dichloromethane, was added 1.94 g of 70% m-chloroperoxybenzoic acid. The reaction mixture was stirred at 0° C. for 2 hours. Then 40 ml 5% aqueous sodium bicarbonate was added to the solution and the solution was stirred for 10 minutes. The solution was extracted with dichloromethane (50 ml×3). The organic layer was concentrated in vacuo and was purified by column chromatography (hexane/ethylacetate=1:1) to give 978 mg of 5-{2-chloro-4-(methylsulfinyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone as a solid. mp: 135-136° C. NMR: δ1.59 (s, 6H), 2.78 (s, 3H), 7.22 (m, 3H), 7.25 (m, 2H), 7.54 (m, 2H), 7.79 (m, 1H). IR (cm−1): 1698, 1623, 1392, 1242, 1145, 1063.

Workup

  1. stirringthe solution was stirred for 10 minutes
  2. extractionThe solution was extracted with dichloromethane (50 ml×3)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customwas purified by column chromatography (hexane/ethylacetate=1:1)

Sources & evidence

ORD record
ord-4a59d80eb6a24041bc75d4b83d9fcf79
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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