Reaction #1777

Reaction equation

3-chloromethyl-2-methylpyridine

m-chloroperoxybenzoic acid

→

3-Chloromethyl-2-methylpyridine N-oxide

Solvents

CHCl3

Conditions

Workup

1. 1
   ExtractionThe solution was extracted with equal volumes of saturated aqueous NaHCO3 and water
2. 2
   Dryingdried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated under reduced pressure
5. 5
   OtherThe residue was purified by pressurized silica gel column chromatography

Procedure

To a stirred solution of 3-chloromethyl-2-methylpyridine from Step 2 above (0.50 g; 3.5 mmol) in CHCl3 (40 mL) was added m-chloroperoxybenzoic acid (1.1 g of 55:45 mCPBA:mCBA; 3.5 mmol). After 1.5 h, TLC analysis indicated complete conversion to a lower Rf product. The solution was extracted with equal volumes of saturated aqueous NaHCO3 and water, dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 97:3 CH2Cl2 :MeOH as eluant. 3-Chloromethyl-2-methylpyridine N-oxide was obtained as a solid (TLC: Rf =0.30 (97:3 CH2Cl2 :MeOH); FAB MS m/z 158 (M+ +H)).

Source