Sodium hydride → 1-Tert-butyl 3-ethyl 2-(6-nitropyridin-3-yl)malonate

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (60% in oil, 0.650 g, 16.4 mmol) in DMF (40 mL) was added tert-butyl ethyl propanedioate (2.8 g, 15.1 mmol) at room temperature. The mixture was stirred for 30 min. A solution of 5-chloro-2-nitropyridine (2.00 g, 12.6 mmol) in DMF (10 mL) was added. The mixture was heated to 80° C. and stirred for 4 hours. The solvent was removed under reduce pressure. Water was added and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatography with silica gel to give tert-butyl ethyl (6-nitropyridin-3-yl)propanedioate.

Provenance & Evidence