Hydrochloric Acid → Dibenzyl 5-nitro-2-pyridylmalonate

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Reaction Steps

A solution of dibenzyl malonate (2.84 g, 10 mmol) in THF (10 ml) was gradually dropped to sodium hydride (800 mg, 20 mmol: 60%) in THF (20 ml) under a nitrogen atmosphere at room temperature. After cessation of evolution of hydrogen, thereto was gradually added 2-chloro-5-nitropyridine (1.59 g, 10 mmol) in THF (10 ml). The mixture was stirred for 24 hours at room temperature, and then neutralized with 1N hydrochloric acid. The resulted precipitate was dissolved by adding ethyl acetate (200 ml) thereto. The aqueous layer was separated and the organic layer was washed with saturated brine (30 mL), followed by concentration in vacuo. The residue was washed with hexane (50 mL×2) and dried to give the object compound (8) as an orange solid (3.29 g, yield 81%).

Provenance & Evidence