Sodium hydride → HCID 20535521, compound

Participants

Reaction Steps

To a solution of 4.8 g of sodium hydride (50% oily suspension) in 130 ml of dimethylformamide, was added dropwise 13.6 g of 3-methylphenethyl alcohol in 20 minutes, and the resultant mixture was heated at 60° C. for 2 hours. After cooling, a solution of 15.9 g of 2-chloro-5-nitropyridine in 80 ml of dimethylformamide was added dropwise thereto at a temperature below 20° C. under ice-cooling. After standing at room temperature overnight, the reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The extracts were washed with water and dried over magnesium sulfate. The oily products were purified by column chromatography on silica gel using benzene as an eluent to give 20.4 g of 2-(3-methylphenethyloxy)-5-nitropyridine as white crystals. M.P., 73.5°-74.5° C.

Provenance & Evidence