Tetrahydrofuran → (1,1-Dimethylprop-2-ynyloxy)acetic acid methyl ester

Temperature

0 °C

A mechanically stirred suspension of sodium hydride (60% dispersion in mineral oil, 10.0 g, 0.25 mol) in THF (170 mL) at 0° C. under N2 gas was treated with 2-methyl)-3-butyn-2-ol (29.1 mL, 0.30 mol) in THF (70 mL) dropwise. After stirring at 0° C. for 1 hour, the reaction mixture was treated with methyl bromoacetate (35.5 mL, 0.38 mol) in THF (100 mL). After stirring at ambient temperature overnight, the mixture was quenched into 1 M 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 tittle compound (10.0 g). 1H NMR (CDCl3) δ 1.52 (s, 6H), 2.47 (s, 1H), 3.77 (s, 3H), 4.25 (s, 2H).

1. stirringAfter stirring at ambient temperature overnight
2. customthe mixture was quenched into 1 M 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-c31eba4492c74abc8b085096d3281944

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06538004B2