Propargyl bromide → 2-(2-(Propyn-2-yloxy)ethoxy)ethanol

To a suspension of sodium hydride (60% dispersion in mineral oil) (23 mmol) in dry THF (20 mL) at 0° C. under nitrogen was added a THF solution (100 mL) of diethylene glycol (110 mmol) over 0.5 h. The resultant reaction mixture was allowed to stir at room temperature for 1 h. This was followed by the addition of propargyl bromide (21 mmol). The reaction mixture was then heated under reflux for 8 h. Following this, the reaction was cooled, concentrated in vacuo and diluted with water (30 mL). The mixture was then extracted with ethyl acetate (3×50 mL). The organics were combined, dried over sodium sulfate and the concentrated under vacuum to furnish a crude residue. This was subjected to column chromatography using hexanes and ethyl acetate to afford 22 as a clear oil. Yield 2.1 g (71%).

1. customThe resultant reaction mixture
2. temperatureThe reaction mixture was then heated
3. temperatureunder reflux for 8 h
4. temperaturewas cooled
5. concentrationconcentrated in vacuo
6. additiondiluted with water (30 mL)
7. extractionThe mixture was then extracted with ethyl acetate (3×50 mL)
8. dry with materialdried over sodium sulfate
9. concentrationthe concentrated under vacuum
10. customto furnish a crude residue

ORD record

ord-e9bbe766ac2a4012af3cbb84d8c5eea1

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461171B2