Alkylation of TEB Acetylide Using Tosylates

Abstract

Alkylated products of 3,3,4,4-tetraethoxybut-1-yne (TEB) where prepared from alkylation of the TEB acetylide with a selection of alkyl tosylates, obtained by tosylation of the corresponding tosylates, and alkyl iodides in low to moderate yields (21-66%). Optimization of the reaction conditions where carried out through several sequental reactions, with systematic alterations to every consecutive reaction to achieve the required reaction conditions to afford the expected products. The difference in reactivity of the alkyl tosylates and similar alkyl iodides towards the TEB acetylide is adressed.