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

HRID 496617Notes

Reaction equation

HRID 496617 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-efb660b250cd49f29ecb9d74f7a6e876
Source dataset
uspto-grants-2005_09
Patent number
US06946467B2

Reaction notes

Loading…