Tetrahydrofuran → HCID 22666345, compound

Temperature

60 °C

A solution of 6-vinylbenzo[b]thiophene (2.124 g, 13.3 mmol) in 80 mL THF was added to a solution of 9-borabicyclo[3.3.1]nonane (9-BBN) (5.21 g, 21.3 mmol) in 80 mL THF, rinsing with 5 mL THF. The solution was heated at 60° C. for 2.5 h and then a solution of H2O2 (36 mL, 35%)/NaOH (36 mL. 0.5 M)/H2O (9 mL) was added slowly. The reaction was then heated to 85° C. for 1 h, cooled to room temperature and 50 mL H2O was added. The mixture was extracted with ethyl acetate (3×50 mL), the combined organic solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (2.338 g, 99%).

1. washrinsing with 5 mL THF
2. additiona solution of H2O2 (36 mL, 35%)/NaOH (36 mL. 0.5 M)/H2O (9 mL) was added slowly
3. temperatureThe reaction was then heated to 85° C. for 1 h
4. temperaturecooled to room temperature
5. addition50 mL H2O was added
6. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
7. washthe combined organic solution was washed with brine
8. dry with materialwas dried (Na2SO4)
9. filtrationfiltered
10. customevaporated
11. customPurification by flash chromatography (ethyl acetate/hexanes)

ORD record

ord-2b86b33e27cd430cac46ad4ab590b022

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394273B2