Hydrochloric Acid → HCID 59714955, compound

To an ice-cooled solution of methyl (1-vinylcyclobutyl)acetate (0.67 g) in tetrahydrofuran (3 mL) was added 0.5M9-borabicyclo[3.3.1]nonane/tetrahydrofuran (17.5 mL) dropwise over 10 minutes. The reaction solution was then allowed for its temperature to rise to room temperature and it was stirred for additional 9 hours. The reaction solution was again ice-cooled and ethanol (4 mL), a 6N aqueous sodium hydroxide solution (8 mL) and 30% hydrogen peroxide (8 mL) were successively added thereto. The reaction solution was then allowed for its temperature to rise to room temperature and it was stirred for additional 30 minutes. The reaction solution was again ice-cooled. After conc. hydrochloric acid (5 mL) was added to the solution, it was stirred for additional 30 minutes. The reaction solution was extracted with tert-butyl methyl ether. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (9:1)] to give the title compound (0.31 g).

1. additionwas added 0
2. customto rise to room temperature
3. temperaturecooled
4. customto rise to room temperature
5. stirringit was stirred for additional 30 minutes
6. temperaturecooled
7. stirringwas stirred for additional 30 minutes
8. extractionThe reaction solution was extracted with tert-butyl methyl ether
9. washThe organic layer was washed with saturated aqueous sodium chloride solution
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated under reduced pressure
12. customThe resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (9:1)]

ORD record

ord-43c1cd2b3bba464cb338bada5c2edf5e

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375115B2