m-Chloroperbenzoic acid → HCID 18385736, compound

HRID 2298328Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To 241 mg of 2,2-dimethyl-5-{2-fluoro-4-(methylthio)phenyl}-4-phenyl-3(2H)-furanone (Example 314) dissolved in 50 ml dichloromethane, was added 138 mg of 70% m-chloroperoxybenzoic acid. The mixture was stirred at 0° C. for 1.5 hours, which was followed by addition of 30 ml 5% aqueous sodium bicarbonate. Then the mixture was stirred for 10 minutes and the volatile material was removed in vacuo. The resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3). The organic layer was concentrated under reduced pressure, and then was purified by column chromatographic separation (hexane/ethylacetate=1:1) to afford 187 mg of 2,2-dimethyl-5-{2-fluoro-4-(methylsulfinyl)phenyl}-4-phenyl-3(2H)-furanone as a solid. mp: 149-150° C. NMR: δ1.55 (s, 6H), 2.78 (s, 3H), 7.26 (m, 5H), 7.47 (m, 2H), 7.69 (dd, J=8.4, 6.6 Hz, 2H). IR (cm−1): 1700, 1621, 1380, 1223, 1161, 1075.

Workup

stirringThen the mixture was stirred for 10 minutes
customthe volatile material was removed in vacuo
extractionThe resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3)
concentrationThe organic layer was concentrated under reduced pressure
customwas purified by column chromatographic separation (hexane/ethylacetate=1:1)

Sources & evidence

ORD record: ord-54d0fda5077b47ea9e7c25c9e7485e9f
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492416B1

Reaction notes

Loading…