Iodine → HCID 57779776, compound

Temperature

-10 °C

An oven-dried round-bottom flask containing the product of Step 4 (1.92 g, 8.68 mmol) was fitted with a stirbar and septa and flushed with nitrogen. Dichloromethane (50 mL) and N,N′,N′-tetramethylethylenediamine (5.80 mL, 38.4 mmol) were added, giving a solution that was cooled to −10° C. Iodotrimethylsilane (4.80 mL, 35.3 mmol) was added, and stirring was continued at −10° C. for 30 minutes. Iodine (4.71 g, 18.6 mmol) was then added, and the reaction was warmed to 0° C. After stirring 2 hours at 0° C., the reaction was diluted with dichloromethane (100 mL) and washed with 10% aqueous sodium sulfite solution (2×50 mL). The organic layer was then dried over MgSO4, filtered and concentrated in vacuo to give an oil that was purified via flash chromatography on silica gel (0% to 30% ethyl acetate/hexanes linear gradient) to give the desired product.

1. customwas fitted with a stirbar and septa
2. customflushed with nitrogen
3. customgiving a solution that
4. temperaturethe reaction was warmed to 0° C
5. stirringAfter stirring 2 hours at 0° C.
6. washwashed with 10% aqueous sodium sulfite solution (2×50 mL)
7. dry with materialThe organic layer was then dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give an oil that
11. customwas purified via flash chromatography on silica gel (0% to 30% ethyl acetate/hexanes linear gradient)

ORD record

ord-ad12be14b6024febaf186103740a92b5

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888345B2