Réaction #1777

Équation de réaction

3-chloromethyl-2-methylpyridine

m-chloroperoxybenzoic acid

→

3-Chloromethyl-2-methylpyridine N-oxide

Solvants

CHCl3

Conditions de réaction

Traitement

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

Mode opératoire

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