Реакция #1777

Уравнение реакции

3-chloromethyl-2-methylpyridine

m-chloroperoxybenzoic acid

→

3-Chloromethyl-2-methylpyridine N-oxide

Растворители

CHCl3

Условия реакции

Обработка

1. 1
   ЭкстракцияThe solution was extracted with equal volumes of saturated aqueous NaHCO3 and water
2. 2
   Сушкаdried (MgSO4)
3. 3
   Фильтрацияfiltered
4. 4
   Другоеevaporated under reduced pressure
5. 5
   ДругоеThe residue was purified by pressurized silica gel column chromatography

Методика

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)).

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