Reaktion #1777

Reaktionsgleichung

3-chloromethyl-2-methylpyridine

m-chloroperoxybenzoic acid

→

3-Chloromethyl-2-methylpyridine N-oxide

Lösungsmittel

CHCl3

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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)).

Quelle