Hydrochloric Acid → Tricyclo[8.2.1.03,8]trideca-3,5,7-trien-13-one

Ethyl diisopropylamine (10.3 g, 13.9 mL, 79.8 mmol) and a solution of 1-pyrrolidino-1-cyclopentene (5.2 g, 5.5 mL, 37.8 mmol) in acetonitrile (75 mL) were added successively to a vigorously stirred solution of α,α′-dibromo-o-xylene (10.0 g, 38.0 mmol) in acetonitrile (75 mL) and the resultant mixture was heated to reflux under nitrogen for 18 hours. Water (75 mL) was added and the mixture was heated for an addition 1 hour. Then the solution was cooled and 10% hydrochloric acid (38 mL) was added. Most of the volatiles were removed in vacuo, and the resultant residue was extracted with ether (4×100 mL). The combined ethereal extracts were washed successively with brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified using flash column chromatography (“FCC”) to provide 11-oxo-5,6,7,8,9,10-hexahydro-6,9-methanobenzocyclooctene (5.1 g, 72%).

1. temperatureto reflux under nitrogen for 18 hours
2. temperaturethe mixture was heated for an addition 1 hour
3. temperatureThen the solution was cooled
4. customMost of the volatiles were removed in vacuo
5. extractionthe resultant residue was extracted with ether (4×100 mL)
6. washThe combined ethereal extracts were washed successively with brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe concentrate was purified

ORD record

ord-999e85e4d1a349c281e3b0335df3a17f

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056857B2