m-Chloroperbenzoic acid → 4-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-1-oxo-1lambda~5~-pyridine

HRID 586355Notes

Reaction equation

HRID 586355 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][N+:14]([O-:25])=[CH:15][CH:16]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 223216194-(Tert-butyldimethylsilyloxyethyl)-pyridine

Product 1

HCID 197577894-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-1-oxo-1lambda~5~-pyridineYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-(tert-Butyldimethylsilyloxy)ethyl]pyridine (15.2 g, 64 mmol) was dissolved in CH2Cl2 (200 mL). To this solution, m-chloroperbenzoic acid was added and the solution stirred at room temperature for 72 h. The solution was washed with aqueous NaOH (1 M) and layers separated. The water layer was extracted with CH2Cl2. The organic layers were combined, dried (K2CO3), filtered and concentrated under vacuum to provide 4-[2-(tert-butyldimethylsilyloxy)ethyl]pyridine-N-oxide (13.4 g, 83%).

Workup

  1. washThe solution was washed with aqueous NaOH (1 M) and layers
  2. customseparated
  3. extractionThe water layer was extracted with CH2Cl2
  4. dry with materialdried (K2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-15282d92c34d4f75b636ffd906ba8871
Source dataset
uspto-grants-2005_08
Patent number
US06936611B2

Reaction notes

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