Sodium Iodide → HCID 67468122, compound

Temperature

80 °C

To a suspension of 1H-[1,2,3]triazole (2.0 g, 29 mmol), potassium carbonate (4.6 g, 33.4 mmol, 1.15 eq.) and sodium iodide (4.3 g, 29 mmol, 1.0 eq.) in acetonitrile (50 mL) was added a solution of (2-bromo-ethoxy)-tert-butyl-dimethyl-silane (7.80 g, 33 mmol) in acetonitrile (7 mL). The resulting mixture was heated to 80° C. for 5 hr under an atmosphere of nitrogen. The mixture was cooled and filtered. The filtrate was evaporated under reduced pressure and the resulting residue partitioned between heptane (200 mL) and water (100 mL). The organic phase was washed with saturated brine solution (30 mL) and dried over sodium sulphate. The resulting mixture was filtered and the filtrate evaporated under reduced pressure to give an oil. This oil was was purified by chromatography on silica gel (100 g) eluting with a gradient of ethyl acetate in heptane (0:100 to 50:50) to give the title compound as a colourless oil (2.9 g, 44%).

1. temperatureThe mixture was cooled
2. filtrationfiltered
3. customThe filtrate was evaporated under reduced pressure
4. customthe resulting residue partitioned between heptane (200 mL) and water (100 mL)
5. washThe organic phase was washed with saturated brine solution (30 mL)
6. dry with materialdried over sodium sulphate
7. filtrationThe resulting mixture was filtered
8. customthe filtrate evaporated under reduced pressure
9. customto give an oil
10. customThis oil was was purified by chromatography on silica gel (100 g)
11. washeluting with a gradient of ethyl acetate in heptane (0:100 to 50:50)

ORD record

ord-06dd19dc0ba8422692e21c5a8b6720a0

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916593B2