Hydrochloric Acid → Methyl 2-(prop-2-yn-1-yloxy)acetate

Participants

Reaction Conditions

Reaction Steps

A mechanically stirred suspension of sodium hydride (60 5% dispersion in mineral oil) (50 g, 1.25 mol) in tetrahydrofuran (800 mL) at 0° C. under nitrogen was treated dropwise with a solution of propargyl alcohol (84 g, 1.5 mol) in tetrahydrofuran (175 mL), stirred at 0° C. for 1 hour, treated with a solution of methyl bromoacetate in tetrahydrofuran (250 mL) over 15 minutes, stirred at 0° C. for 30 minutes, stirred at ambient temperature for 2 hours, and treated with 2M HCl (800 mL). The organic layer was isolated and the aqueous layer was extracted with ethyl acetate (2×, 500 mL). The combined organic layers were washed with brine (200 mL), dreid (MgSO4), filtered, concentrated and distilled (bp 75-85° C. at 20 torr) to provide the title compound (83 g).

Provenance & Evidence