Diethyl Oxalate → Ethyl 3-(2-chloro-5-nitropyridin-4-yl)-2-oxopropanoate

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Reaction Steps

Route B: To a solution of 2-chloro-4-methyl-5-nitropyridine (1.0 g, 5.8 mmol) in diethyl oxalate (4.23 g, 29 mmol) under an argon atmosphere was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.95 mL, 6.4 mol). The mixture was stirred at rt for 1.5 h then diluted with t-butyl methyl ether (40 mL), water (30 mL) and acetic acid (1 ml). The organic layer was separated, washed with water, dried (MgSO4) and evaporated to dryness. The resultant damp red solid residue was finally dried under high vacuum at 40–50° C. to give the title compound.

Provenance & Evidence