반응 #1776

반응 방정식

3-hydroxymethyl-2-methylpyridine

3-Hydroxymethyl-2-methylpyridine

SOCl2

→

3-chloromethyl-2-methylpyridine

용매

CH2Cl2

반응 조건

후처리

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

실험 절차

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)).

출처