Reaction #1776

Reaction equation

3-hydroxymethyl-2-methylpyridine

3-Hydroxymethyl-2-methylpyridine

SOCl2

→

3-chloromethyl-2-methylpyridine

Solvents

CH2Cl2

Conditions

Workup

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

Procedure

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)).

Source