Sodium hydride → tert-Butyl ethyl (5-nitropyridin-2-yl)malonate

Participants

Reaction Steps

To a stirred suspension of 2-chloro-5-nitropyridine (7.66 g, 48.3 mmol), sodium hydride (60% in mineral oil, 2.13 g, 53.1 mmol) in N,N-dimethylformamide (100 mL) was added tert-butyl ethyl malonate (10.0 g, 53.1 mmol) dropwise at room temperature, and the mixture was stirred at room temperature for 20 h. The mixture was washed with water (300 mL×5), brine (100 mL), dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (5:1) to give 12.3 g (82%) of the title compound as a brown oil.

Provenance & Evidence