Methanol → Dimethyl pyridine-2,4-dicarboxylate

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Reaction Steps

PCl5 (39 g; 0.186 mol; 3 eq) and pyridine-2,4-dicarboxylic acid (11.5 g; 6.2×10−2 mol) are introduced into a 500 mL flask. The mixture is stirred at ambient temperature for 45 minutes: it forms a green liquid. It is then diluted with dichloromethane (80 mL) then methanol is added (20 mL) with caution. The whole is poured into water H2O (300 mL) containing 60 g of NaHCO3, the aqueous phase is washed with dichloromethane (4×50 mL) and the organic phase is washed with 1M Na2CO3 (2×50 mL). The crude product is purified by flash chromatography (eluent: 75:25 AcOEt/cyclohexane).

Provenance & Evidence