Reacción #1777

Ecuación de reacción

3-chloromethyl-2-methylpyridine

m-chloroperoxybenzoic acid

→

3-Chloromethyl-2-methylpyridine N-oxide

Disolventes

CHCl3

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe solution was extracted with equal volumes of saturated aqueous NaHCO3 and water
2. 2
   Secadodried (MgSO4)
3. 3
   Filtraciónfiltered
4. 4
   Otroevaporated under reduced pressure
5. 5
   OtroThe residue was purified by pressurized silica gel column chromatography

Procedimiento

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)).

Fuente