反应 #1776

反应方程式

3-hydroxymethyl-2-methylpyridine

3-Hydroxymethyl-2-methylpyridine

SOCl2

→

3-chloromethyl-2-methylpyridine

溶剂

CH2Cl2

反应条件

后处理

1. 1
   其他the solvent and excess SOCl2 were evaporated under reduced pressure
2. 2
   其他The residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3
3. 3
   其他The organic layer was separated
4. 4
   洗涤the aqueous layer was washed with additional CH2 Cl2 (2×40 mL)
5. 5
   其他The combined organic layers were evaporated under reduced pressure

实验过程

To a stirred solution of 3-hydroxymethyl-2-methylpyridine from Step 1 above (1.00 g, 8.13 mmol) in 40 mL of CH2Cl2 at ambient temperature was added SOCl2 (9.0 mL, 123 mmol). The reaction mixture was stirred for 4 hours, and the solvent and excess SOCl2 were evaporated under reduced pressure. The residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic layer was separated, and the aqueous layer was washed with additional CH2 Cl2 (2×40 mL). The combined organic layers were evaporated under reduced pressure to give 3-chloromethyl-2-methylpyridine as a pale yellow-brown solid (TLC: Rf =0.85 in 5% MeOH in CH2Cl2 ; FAB MS m/z 142 (M+ +H)).

来源