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