Thionyl Chloride → HCID 19831103, compound

Participants

Reaction Steps

Starting from 3-chloro-4-pyridine carbonitrile, by reaction with 4-chlorobenzyl alcohol in the presence of sodium hydride in dimethylformamide, 3-(4-chlorobenzyloxy)-4-pyridine carbonitrile is obtained, which is reacted with butyllithium in diethyl ether to 3-(4-chlorobenzyloxy)-4-valeryl pyridine. The keto group of this 4-valeryl derivative is reduced with sodium boron hydride to the hydroxyl group; 1-[3-(4-chlorobenzyloxy)-4-pyridyl]-1-pentanol is obtained. The hydroxyl group of the pentanol derivative is exchanged with thionyl chloride in methylene chloride for a chlorine group, 3-(4-chlorobenzyloxy)-4-(1-chloropentyl)-pyridine is obtained. By subsequent reaction with imidazole in the presence of sodium hydride (analogously to example 13), the 3-(4-chlorobenzyloxy)-4-[1-(1-imidazolyl)-pentyl]-pyridine is obtained.

Provenance & Evidence