Propargyl-3-sulfopropyl ether sodium salt is prepared by the reaction of 1,3-propanesultone and propargyl alcohol. The specific synthesis steps are as follows:
To a chilled (5 °C) slurry of NaH (60% in mineral oil, 1.60 g, 40.9 mmol, 1.0 equiv.) in dry DMF (30 mL) was added dropwise a solution of propargyl alcohol (2.4 mL, 40.9 mmol, 1.0 equiv.) in dry DMF (30 mL) over a ten minute period. I ,3-Propanesultone (5.0 g, 40.9 minol, 1.0 equiv.) was dissolved in dry DMF (30mL), and the resulting solution added dropwise over a five minute period to the chilled sodium propargylate solution. After stirring for ten minutes in the ice bath, the flask was transferred to an oil bath and heated at 60°C for three hours. Most of the DMF was then removed by rotavap, and the remaining oil was triturated with 200 mL diethyl ether to yield a white solid, which was collected by vacuum filtration. The product was driedunder vacuum to provide Propargyl-3-sulfopropyl ether sodium salt as a white powder (7.4 g, 90%).
