SYNTHESIS OF 1-HALOPHENYL 4-(2-IMIDAZOLYL)-1-BUTANONES AND 5-(2-IMIDAZOLYL)-1-PENTANONES AND THEIR KETALIZATION WITH GLYCEROL

An alternate synthesis of -(2,4-dichlorophenyl)-4-(2-imidazolyl)-1-but anones 5d is presented after 1-[(dimethylamino)methyl- and l-methyl]-2 -lithioimidazole failed to be substituted satisfactorily by 2,4-dichlo rophenyl)-2-(3-iodopropyl)-1,3-dioxolane (3b). The Pinner addition of ethanol to ,4-dichlorophenyl)-2-(3-cyanopropyl)-1,3-dioxolane yielded the corresponding imidate which was reacted with 1-amino-2,2-dimethoxy ethane to form an amidine. Hot dilute hydrochloric acid converted this amidine to the 2-imidazolyl ketone 5b. Syntheses of homologous 1-(4-c hloro- and 2,4-dichlorophenyl)-4-(2-imidazolyl)-1-pentanones 20 are de scribed. Ketalizations of 5 and 20 with glycerol formed imidazolyl 1,3 -dioxolanyl alcohols. Selective N- and O-alkylations of some of these imidazolyl alcohols are described.