تفاعل #1777

معادلة التفاعل

3-chloromethyl-2-methylpyridine

m-chloroperoxybenzoic acid

→

3-Chloromethyl-2-methylpyridine N-oxide

المذيبات

CHCl3

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe solution was extracted with equal volumes of saturated aqueous NaHCO3 and water
2. 2
   تجفيفdried (MgSO4)
3. 3
   ترشيحfiltered
4. 4
   أخرىevaporated under reduced pressure
5. 5
   أخرىThe residue was purified by pressurized silica gel column chromatography

الإجراء التجريبي

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)).

المصدر