143191-54-2Relevant academic research and scientific papers
New general synthesis of α-alkoxyketones via α′- alkylation, α-alkylation and α,α′-dialkylation of α-alkoxyketimines
Colpaert, Filip,Mangelinckx, Sven,Rocchetti, Maria Teresa,De Kimpe, Norbert
experimental part, p. 549 - 558 (2011/02/28)
α-Methoxy- and α-ethoxyketones, as important intermediates in organic synthesis and flavor compounds in food chemistry, were synthesized by deprotonation of N-(1-alkoxy-2-propylidene)isopropylamine, prepared by condensation of the corresponding α-alkoxyacetone with isopropylamine, and subsequent reaction of the corresponding 1-azaallylic anions with alkyl halides to afford α′-alkylated, α-alkylated and α, α′-dialkylated ketimines. Hydrolysis of the imino function led to the desired substituted α-alkoxyketones. The ratio of α-, α′-, and α,α′-(di)alkylated compounds depended on the amount of base used and on the nature of the alkylating reagent.
