m-Chloroperbenzoic acid → HCID 18385842, compound

HRID 2298339Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:25])[C:11]([CH3:24])([CH3:23])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[C:16]([CH3:22])[CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:31].C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:25])[C:11]([CH3:23])([CH3:24])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:21])=[O:31])=[C:16]([CH3:22])[CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 320 mg of 4-(3,5-difluorophenyl)-2,2-dimethyl-5-{3-methyl-4-(methylthio)phenyl}-3(2H)-furanone (Example 381) in 50 ml dichloromethane, was added 172 mg of 70% m-chloroperoxybenzoic acid. The mixture was stirred at 0° C. for an hour, which was followed by addition of 30 ml 5% aqueous sodium bicarbonate. The solution was stirred for another 10 minutes. Then the mixture was concentrated in vacuo, and was extracted with 50 ml water and dichloromethane (30 ml×3). Then the organic layer was concentrated under reduced pressure and was purified by column chromatography (hexane/ethylacetate=1:1) to give 211 mg of 4-(3,5-difluorophenyl)-2,2-dimethyl-5-{3-methyl-4-(methylsulfinyl)phenyl}-3(2H)-furanone. NMR: δ1.57 (s, 6H), 2.36 (s, 3H), 2.73 (s, 3H), 6.77 (m, 1H), 6.86 (m, 2H), 7.50 (m, 1H), 7.66 (m, 1H), 7.99 (d, J=8.4 Hz, 1H). IR (cm−1): 1698,1624,1592,1384, 1310,1206,1072,915.

Workup

stirringThe solution was stirred for another 10 minutes
concentrationThen the mixture was concentrated in vacuo
extractionwas extracted with 50 ml water and dichloromethane (30 ml×3)
concentrationThen the organic layer was concentrated under reduced pressure
customwas purified by column chromatography (hexane/ethylacetate=1:1)

Sources & evidence

ORD record: ord-afdaadfe6bbd43908435505ab526d0d1
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492416B1

Reaction notes

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