Hydrogen Peroxide → 4-(3-(tert-Butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide

HRID 1516894Notes

Reaction equation

HRID 1516894 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=1)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[OH:21]O>ClCCl.C[Re](=O)(=O)=O>[C:14]([O:13][C:11]([C:10]1[CH:9]=[C:8]([C:7]2[CH:6]=[CH:5][N+:4]([O-:21])=[CH:3][C:2]=2[CH3:1])[CH:20]=[CH:19][CH:18]=1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 57895121Tert-butyl 3-(3-methylpyridin-4-yl)benzoate

Product 1

HCID 578951674-(3-(tert-Butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(3-methylpyridin-4-yl)benzoate (0.500 g, 1.86 mmol) was dissolved in a mixture of dichloromethane (0.800 mL) and 30% hydrogen peroxide (0.421 mL). Methyltrioxorhenium (VII) (2.3 mg, 0.92 mmol) was added and the reaction mixture was stirred vigorously for 5 hours. The layers were then separated and the organic layer was treated with sodium sulfite, and then dried over sodium sulfate. The crude product filtered, evaporated to dryness, and used without further purification. ESI-MS m/z calc. 285.1, found 286.1 (M+1)+. Retention time 1.22 minutes.

Workup

  1. customThe layers were then separated
  2. additionthe organic layer was treated with sodium sulfite
  3. dry with materialdried over sodium sulfate
  4. filtrationThe crude product filtered
  5. customevaporated to dryness
  6. customused without further purification

Sources & evidence

ORD record
ord-e9423e8c2d81456d900760a835b65f22
Source dataset
uspto-grants-2012_07
Patent number
US08227615B2

Reaction notes

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