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

Temperature

0 °C

To a stirred suspension of potassium tert-butoxide (1.06 g, 9.42 mmol) in THF (300 mL) cooled to 0° C. in an ice-bath was added a solution of 2,2′-oxydiethanol (4.60 g, 78.0 mmol) in THF (10 mL). The mixture was stirred at 0° C. for 30 min and was then allowed to warm to RT and was treated dropwise with propargyl bromide (1.68 mL of an 80% solution in toluene, 11.30 mmol). The reaction mixture was stirred at RT for 16 hr and diluted with brine and water (5:1, 50 mL) and was extracted with EtOAc (3×500 mL). The combined organic extracts were dried, filtered and evaporated in vacuo. The residue was purified by flash column chromatography, eluting with 25 to 60% EtOAc in heptane, to afford the title compound (10) (410 mg, 30%) as a yellow oil: 1H NMR (250 MHz, CDCl3) δ: 2.22 (1H, s), 2.45 (1H, t), 3.58-3.66 (2H, m), 3.67-3.79 (6H, m), 4.22 (2H, d).

1. temperatureto warm to RT
2. stirringThe reaction mixture was stirred at RT for 16 hr
3. extractionwas extracted with EtOAc (3×500 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 25 to 60% EtOAc in heptane

ORD record

ord-0574e62e08a240628a19dad34b4ebd9f

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741909B2