Hydrochloric Acid → 3-Oxaspiro[5.7]tridecan-2-one

To an ice-cooled solution of methyl (1-vinylcyclooctyl) acetate (1.33 g) in tetrahydofuran (6 mL) was added 0.5M 9-borabicyclo[3.3.1]nonane/tetrahydrofuran (25.3 mL) dropwise over 15 minutes. The reaction solution was then allowed for its temperature to rise to room temperature and it was stirred for additional 2 hours. The reaction solution was again ice-cooled, and ethanol (8 mL), a 6N aqueous sodium hydroxide solution (11 mL) and 30% hydrogen peroxide (11 mL) were successively to the solution. The reaction solution was allowed for its temperature to rise to room temperature and it was stirred for additional 75 minutes. The reaction solution was again ice-cooled. After addition of conc. hydrochloric acid (8 mL), the solution was stirred for additional 30 minutes. The reaction solution was extracted with ethyl acetate. 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 (0.74 g).

1. customto rise to room temperature
2. temperaturecooled
3. customto rise to room temperature
4. stirringit was stirred for additional 75 minutes
5. temperaturecooled
6. stirringthe solution was stirred for additional 30 minutes
7. extractionThe reaction solution was extracted with ethyl acetate
8. washThe organic layer was washed with saturated aqueous sodium chloride solution
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (9:1)]

ORD record

ord-57dec8679771463bb5a8402ebdabed3d

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375115B2