1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-Oxabicyclo[3.2.1]oct-3-en-7-one

To 4-iodo-6-oxabicyclo[3.2.1]octan-7-one (8.00 g, 31.7 mmol) in benzene (100 ml) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (7.9 g, 32 mmol) under nitrogen, and the mixture was heated under reflux for 6 h. The white precipitate was filtered off from the cooled solution and washed with ether (100 ml). The combined filtrates were washed with water (50 ml), 1N HCl (50 ml), and brine (25 ml), and then dried over magnesium sulfate. The solvents were removed by rotary evaporation to afford the alkene as a light brown oil (2.6 g, 66%).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 6 h
3. filtrationThe white precipitate was filtered off from the cooled solution
4. washwashed with ether (100 ml)
5. washThe combined filtrates were washed with water (50 ml), 1N HCl (50 ml), and brine (25 ml)
6. dry with materialdried over magnesium sulfate
7. customThe solvents were removed by rotary evaporation

ORD record

ord-83fa78c7aaf34dd0a13b486242c7214d

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402592B2