Water → 4-[3,5-Difluoro-4-(methylsulfinyl)phenyl]-5-methyl-3-phenylisoxazole
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]2[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:13][O:14][C:15]=2[CH3:16])[CH:5]=[C:6]([F:10])[C:7]=1[S:8][CH3:9].O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:33].[Mg+2].O>ClCCl.CO>[F:10][C:6]1[CH:5]=[C:4]([C:11]2[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:13][O:14][C:15]=2[CH3:16])[CH:3]=[C:2]([F:1])[C:7]=1[S:8]([CH3:9])=[O:33]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-[3,5-difluoro-4-(methylthio)phenyl]-5-methyl-3-phenylisoxazole in dichloromethane (75 mL) and methanol (15 mL) cooled in an ice bath was added magnesium monoperoxyphthalate hexahydrate (4.4 g 80%, 7.1 mmol) in portions over 5 minutes. The reaction mixture was stirred for 90 minutes, then poured into water and extracted with dichloromethane (1×250 mL, 1×75 mL). The combined extracts were washed with dilute ammonium chloride, dried with magnesium sulfate, and concentrated. Purification by silica gel chromatography using 25% ethyl acetate/25% hexanes/50% dichloromethane gave 4-[3,5-difluoro-4-(methylsulfinyl)phenyl]-5-methyl-3-phenylisoxazole as a white solid. 1H NMR (CDCl3/400 MHz) 7.37-7.44 (m, 5H), 6.77-6.81 (m, 2H), 3.13 (s, 3H) 2.50 (s, 3H). HRMS m/z 334.0698 (M+H+, calcd 334.0713). Anal. Calcd for C17H13F2NO2S: C, 61.25; H, 3.93; N, 4.20; Found: C, 61.22; H, 4.00, N 4.02.
Workup
- extractionextracted with dichloromethane (1×250 mL, 1×75 mL)
- washThe combined extracts were washed with dilute ammonium chloride
- dry with materialdried with magnesium sulfate
- concentrationconcentrated
- customPurification by silica gel chromatography
Sources & evidence
- ORD record
- ord-dfc70740e70f49ee837d2e98e1cc606d
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06673818B2
Reaction notes
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