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

Temperature

0 °C

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).

1. stirringAfter stirring at ambient temperature overnight
2. customthe reaction mixture was quenched into 1M HCl (300 mL)
3. extractionextracted with ethyl acetate (3×300 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated to half the volume
6. distillationThe residue was distilled by vacuum distillation (bp. 118-120° C./20 mmHg)

ORD record

ord-19980cee434942149a36a8f44c53a563

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06642222B2