Sodium Carbonate → Methyl 2-(chloromethyl)pyridine-3-carboxylate

참여 물질

반응 단계

Methyl 2-methylpyridine-3-carboxylate 1-oxide (2.93 g, 17.53 mmol) was taken up in POCl3 (17 mL, 182 mmol) and heated to reflux for 3 hours. The mixture was then cooled to room temperature and poured into ice-water. The resulting dark solution was neutralised with solid Na2CO3 and the products extracted into EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (2-30% EtOAc-hexanes) gave methyl 6-chloro-2-methylpyridine-3-carboxylate as a pale yellow oil (A) and methyl 2-(chloromethyl)pyridine-3-carboxylate (B) as an orange oil.

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