Sciencemadness Discussion Board

Et3N-MeCN in E2 RXN

bdestrad - 28-3-2016 at 13:31

Is Et3N in acetonitrile (pKa 18.70) sufficient to facilitate an E2 reaction with 1-bromo-4-phenylbutane? Any thoughts on optimization with only these reagents?

clearly_not_atara - 28-3-2016 at 16:08

I think the reaction product is 4-phenylbutyltriethylammonium bromide. Consider (Me3Si)2NLi, although in any variant of this reaction, over-alkylation may be a concern. Using acetonitrile as the solvent may cause self-condensation.