168907-71-9Relevant articles and documents
Synthesis of Aryl 3-(2-Imidazolyl)propyl Ketones.
Davis, Frank S.,Huang, Liang-fu,Bauer, Ludwig
, p. 915 - 920 (2007/10/02)
The approach to the title compounds was via lithiation-substitution of N-methyl or N-(triphenylmethyl)imidazole by some iodo ketals. 4-Chloro-4'-halobutyrophenones (halo = F, Cl, Br) were converted by sodium iodide to the corresponding aliphatic iodides which were subsequently ketalized with ethylene glycol to provide the corresponding iodo ketals.Lithiation of either 1-methyl- or 1-(triphenylmethyl)imidazole with n-butyllithium generated the corresponding 2-lithioimidazoles, in situ, which were then reacted with these iodo ketals to form the corresponding C-2 substitute d imidazoles.Dilute aqueous acid hydrolysis released the ketone from the ketal.For N-triphenylmethyl protected imidazoles, the triphenylmethyl group was also hydrolyzed to give triphenylmethanol and 3-(2-imidazolyl)propyl 4-haloaryl ketones.These N-unsubstituted imidazolyl ketones can be alkylated independently with triphenylmethyl chloride to form the corresponding N-triphenylmethyl imidazole derivatives.