反応 #1776

反応方程式

3-hydroxymethyl-2-methylpyridine

3-Hydroxymethyl-2-methylpyridine

SOCl2

→

3-chloromethyl-2-methylpyridine

溶媒

CH2Cl2

反応条件

後処理

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

実験手順

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)).

出典