Simple approach for the regioselective synthesis of a bis (β-aminoalcohol) derived from polyoxyethylene: first report of fast ring-opening of polyoxyethylene diglycidyl ethers with sodium amide

Abstract

An efficient oxirane ring opening of polyoxyethylene diglycidyl ethers with sodium amide has been achieved for the first time under catalyst-free conditions. This reaction is highly regioselective and affords the corresponding bis (β-aminoalcohols) polyoxyethylene in good yields as a mixture of regioisomers. Various other advantages are associated with this novel protocol, including short reaction time, no need for catalysts, and a simple workup procedure. Here, the wide scope and utility of this method is demonstrated, and the stereochemistry is discussed. The regioisomeric ratio is determined from binomial calculation based on 1H NMR data and is confirmed by GC–MS.