2-Methyl-3-butyn-2-ol → (1,1-Dimethylprop-2-ynyloxy)acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mechanically stirred suspension of sodium hydride (10.0 g, 0.25 mol) in THF (170 mL) at 0° C. under N2 gas was treated dropwise with a solution of 2-methyl-3-butyn-2-ol (29.1 mL, 0.30 mol) in THF (70 mL). After stirring at 0° C. for 1 hour, the reaction mixture was treated at 0° C. with a solution of methyl bromoacetate (35.5 mL, 0.38 mol) in THF (100 mL). After stirring at ambient temperature overnight, the reaction mixture was quenched into 1M HCl (300 mL) and extracted with ethyl acetate (3×300 mL). The organic layers were combined, dried over Na2SO4, and concentrated to half the volume. The residue was distilled by vacuum distillation (bp. 118-120° C./20 mmHg) to provide the title compound (10.0 g).

Provenance & Evidence