Réaction #1776

Équation de réaction

3-hydroxymethyl-2-methylpyridine

3-Hydroxymethyl-2-methylpyridine

SOCl2

→

3-chloromethyl-2-methylpyridine

Solvants

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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