Реакция #1776

Уравнение реакции

3-hydroxymethyl-2-methylpyridine

3-Hydroxymethyl-2-methylpyridine

SOCl2

→

3-chloromethyl-2-methylpyridine

Растворители

CH2Cl2

Условия реакции

Обработка

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

Методика

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)).

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