Propargyl alcohol → 3-[2-(2-Methoxyethoxy)ethoxy]prop-1-yne

Temperature

5 °C

To a stirred suspension of sodium hydride (3.12 g, 78.0 mmol) in THF (100 mL) cooled to 5° C. in an ice-bath was added a solution of propargyl alcohol (4.60 g, 78.0 mmol) in THF (20 mL) drop-wise. The mixture was stirred at 5° C. for 30 min and was then allowed to warm to RT and treated dropwise with 1-bromo-2-(2-methoxyethoxy)ethane (7.00 mL, 52.0 mmol). The reaction mixture was stirred at RT for 16 hr and was then, diluted with water (100 mL) and extracted with diethyl ether (2×100 mL). The combined organic extracts were dried, filtered and evaporated in vacuo. The residue was purified by flash column chromatography, eluting with 30% EtOAc in heptane, to afford the title compound (9) (250 mg, 9%) as a colourless oil: 1H NMR (500 MHz, MeOD) δ: 4.18 (2H, d), 3.66-3.69 (2H, m), 3.60-3.66 (4H, m), 3.52-3.56 (2H, m), 3.36 (3H, s), 2.84 (1H, t).

1. temperatureto warm to RT
2. stirringThe reaction mixture was stirred at RT for 16 hr
3. extractionextracted with diethyl ether (2×100 mL)
4. customThe combined organic extracts were dried
5. filtrationfiltered
6. customevaporated in vacuo
7. customThe residue was purified by flash column chromatography
8. washeluting with 30% EtOAc in heptane

ORD record

ord-8ec4b77bcb9340db8fa2c7aa0bf24c8f

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741909B2