m-Chloroperbenzoic acid → HCID 18385651, compound

HRID 2298335Notes

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution 3.5 g of 5-{3-chloro-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 354) in 80 ml dichloromethane, was added 2.5 g of 70% m-chloroperoxybenzoic acid, and 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 2.43 g of 5-{3-chloro-4-(methylsulfinyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone as a solid. mp: 120-121° C. NMR: δ1.57 (s, 6H), 2.84 (s, 3H), 7.30 (m, 3H), 7.38 (m, 2H), 7.72 (s, 1H), 7.74 (d, J=8.1 Hz, 1H), 7.91 (d, J=8.1 Hz, 1H). IR (cm−1): 1699, 1619, 1319, 1239, 1169, 1145, 1068.

Workup

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

Sources & evidence

ORD record: ord-b8af012dc3354b9a9c933691a9e42551
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492416B1

Reaction notes

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