Sodium hydride → 2-[2-(4-Chlorophenyl)ethoxy]-5-nitropyridine

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Reaction Steps

To a stirred mixture of NaH (0.77 g) and DMSO is slowly added 4-chlorophenethyl alcohol (5 g) in DMSO (20 ml) while maintaining the temperature at or below 32°. After gas evolution stops, 2-chloro-5-nitropyridine (4 g) is added in small portions while maintaining temperature below 25°. After stirring about 1 hour, the reaction is poured onto about 300 g ice and then filtered. The solid is dissolved in ether, washed with water, dried (sodium sulfate) and solvent evaporated to give 2-(4-chlorophenethoxy)-5-nitropyridine, a grey solid.

Provenance & Evidence