Hydrogen Peroxide → 2-(3-(Tert-butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide
Reaction equation
[CH3:1][C:2]1[C:3]([C:8]2[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=2)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:4][CH:5]=[CH:6][CH:7]=1.[OH:21]O>ClCCl.C[Re](=O)(=O)=O>[C:14]([O:13][C:11]([C:10]1[CH:9]=[C:8]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N+:4]=2[O-:21])[CH:20]=[CH:19][CH:18]=1)=[O:12])([CH3:17])([CH3:15])[CH3:16]Participants
Procedure
tert-Butyl 3-(3-methylpyridin-2-yl)benzoate (49.6 g, 184 mmol) was dissolved in a mixture of 75 mL of dichloromethane and 40 mL of 30% hydrogen peroxide. Methyltrioxorhenium (VII) (2.35 g, 9.44 mmol) was added and the reaction mixture was stirred vigorously for 16 hours. The layers were then separated and the organic layer was treated with sodium sulfite and then dried over sodium sulfate. The crude product was then poured onto a pad of silica gel and washed with ethyl acetate. The product was then eluted from the silica gel pad with a mixture of 10% (v/v) methanol in ethyl acetate to yield 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide (29.8 g, 57%) as a white solid. ESI-MS m/z calc. 285.1, found 286.1 (M+1)+. Retention time 1.22 minutes.
Workup
- customThe layers were then separated
- additionthe organic layer was treated with sodium sulfite
- dry with materialdried over sodium sulfate
- additionThe crude product was then poured onto a pad of silica gel
- washwashed with ethyl acetate
- washThe product was then eluted from the silica gel pad with a mixture of 10% (v/v) methanol in ethyl acetate
Sources & evidence
- ORD record
- ord-1ea3abeb83bf43d5bffc283befb2b9e6
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07754739B2
Reaction notes
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