A facile preparation of 2-(2-hydroxyethyl)homoallenylsilanes using in situ generated homoallenylindium reagent

초록

In situ generated homoallenylindium reagents derived from the reaction of indium with 4-bromo-3-[(trimethylsilyl)methyl]-1,2-1,2-butadiene reacted with a variety of aldehydes in DMF to produce 2-(2-hydroxyethyl)homoallenylsilanes at room temperature in good to excellent yields. 2- or 3-Hydroxybenzaldehyde that contains labile hydrogen was reacted with homoallenylindium reagent to provide the homoallenylsilanes. In the case of 4-formylbenzoic acid, the desired compound was produced in 88% yield. 4-Bromo-3-[(trimethylsilyl)methyl]-1,2-butadiene was prepared from monoacetylation and mesylation of 2-butyn-1,4-diol, addition of trimethylsilylmethyl anion, saponification and mesylation followed by Finkelstein reaction.

키워드