Réaction #2247

Équation de réaction

2-chloro-4-cyano-pyridine

methyl-magnesium chloride

HCl

diethyl ether

→

4-acetyl-2-chloro-pyridine

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred for 14 h at RT
2. 2
   ExtractionExtraction with diethyl ether and methylene chloride
3. 3
   Séchagedrying with MgSO4 and concentration

Mode opératoire

24.61 g (177.62 mmol) of 2-chloro-4-cyano-pyridine are placed in 1.25 litres of diethyl ether under nitrogen, and 120 ml (22% in tetrahydrofuran, 353 mmol) of methyl-magnesium chloride are added. The red suspension is stirred for 40 h at RT, poured onto 1.25 litres of ice/water and 250 ml of 6N HCl and stirred for 14 h at RT. Extraction with diethyl ether and methylene chloride, drying with MgSO4 and concentration give 4-acetyl-2-chloro-pyridine; Rf =0.5 (methylene chloride:methanol=9:1).

Source