2,4-Dichlorobenzyl chloride → HCID 20365307, compound

Participants

Reaction Conditions

Reaction Steps

trans-1-[2-Hydroxy-4-phenylbut-3-enyl]imidazole (430 mg.) in 5 ml. dry tetrahydrofuran was treated under nitrogen with stirring with 96 mg. of sodium hydride (56% dispersion in mineral oil) and the mixture heated under reflux for 30 minutes. After cooling in an ice bath the mixture was treated with stirring with 430 mg. of α,2,4-trichlorotoluene in 5 ml. tetrahydrofuran for 30 minutes at 0° C., one hour at 25° C. and overnight under reflux. The resulting mixture was evaporated to dryness, ether (150 ml.) added and the ether extract washed with water, dried over magnesium sulfate and evaporated to afford trans-1-[2-(2,4-dichlorobenzyloxy)-4-phenylbut-3-enyl]imidazole. The nitrate salt precipitated from ether and was crystallized from ethyl acetate, m.p. 133.5°-134.5° C. (foaming).

Provenance & Evidence