反応 #1777

反応方程式

3-chloromethyl-2-methylpyridine

m-chloroperoxybenzoic acid

→

3-Chloromethyl-2-methylpyridine N-oxide

溶媒

CHCl3

反応条件

後処理

1. 1
   抽出The solution was extracted with equal volumes of saturated aqueous NaHCO3 and water
2. 2
   乾燥dried (MgSO4)
3. 3
   ろ過filtered
4. 4
   その他evaporated under reduced pressure
5. 5
   その他The residue was purified by pressurized silica gel column chromatography

実験手順

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)).

出典