Hydrochloric Acid → Methyl [(1-methyl-2-propynyl)oxy]acetate

Participants

Reaction Steps

A mechanically stirred suspension of sodium hydride (60% dispersion in mineral oil, 10 g, 0.25 mol) in tetrahydrofuran (160 mL) at 0° C. under nitrogen was treated with a solution of (±)-3-butyn-2-ol (21 g, 0.30 mol) in tetrahydrofuran (35 mL) over 30 minutes, stirred for 35 minutes, treated with a solution of methyl bromoacetate in tetrahydrofuran (50 mL) over 10 minutes, stirred for 30 minutes at 0° C., stirred at ambient temperature for 16 hours and treated with 2M HCl (150 mL). The organic layer was isolated and the aqueous layer was extracted with ethyl acetate (2×, 100 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered, concentrated and distilled under vacuum to provide the title compound (20 g).

Provenance & Evidence