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Synthesis 1991; 1991(11): 1021-1022
DOI: 10.1055/s-1991-26637
DOI: 10.1055/s-1991-26637
paper
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Expedient Synthesis of 4(5)-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole, the α2-Adrenergic Agonist Medetomidine
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Publication History
Publication Date:
29 April 2002 (online)
(±)-4(5)-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole hydrochloride (5) is prepared in three steps in 79% overall yield from 1-(N,N-dimethylsulfamoyl) imidazole by bis-protection, regioselective lithiation followed by an efficient tandem addition-reduction of the resulting 2,3-dimethylbenzoyl chloride adduct with lithium/ammonia/ammonium chloride.