1-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-one → 1-(4-Chlorobenzyl)-5-(3-methoxybenzoyl)pyridin-2(1H)-one
Reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([CH:13]([OH:22])[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[CH:10]=[CH:9][C:8]2=[O:23])=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13](=[O:22])[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[CH:10]=[CH:9][C:8]2=[O:23])=[CH:24][CH:25]=1Participants
4
Procedure
According to Scheme 7 Method C: 1-(4-Chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)-methyl)pyridin-2(1H)-one (1 eq, 0.28 mmol, 0.10 g, Example 41) and manganese dioxide (30 eq, 8.43 mmol, 0.73 g) were stirred overnight at room temperature in CH2Cl2 (10 mL). Upon completion, the crude mixture was filtered through a pad of celite and the filtrate was concentrated. The crude residue was partitioned between water and CH2Cl2. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over MgSO4 and concentrated under vacuum to afford the title compound as a white solid (0.28 mmol, 0.10 g, 100%).