m-Chloroperbenzoic acid → 2,6-Dimethyl-4-(2-(4 nitrophenyl)ethyl) pyridine N-oxide
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH:5]=[C:4]([CH3:19])[N:3]=1.ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)(Cl)Cl>[CH3:19][C:4]1[CH:5]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH:7]=[C:2]([CH3:1])[N+:3]=1[O-:28]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Compound (3) (22.82 g, 84.5 mmol) was dissolved in chloroform (100 ml), and 16 g (94 mmol) of m-chloroperbenzoic acid (mCPBA) was addedin small portions at RT over a period of 30 min. The mixture was stirred for an additional 2 h and after a negative TLC test for the starting material it was worked up by partitioning between sat. sodium hydrogen carbonate and chloroform. The combined chloroform extracts (3×200 ml) were evaporated yielding a light yellow solid material that was TLC pure.