反应详情

To methyl 5-hexenoate (608 mg) was added 0.5 M 9-bora bicyclo[3.3.1]nonane-tetrahydrofuran solution (9.5 ml) under ice-cooling and the mixture was stirred overnight at room temperature. The reaction mixture was added dropwise to a suspension of tetrahydrofuran (10 ml), (2R)-2-[[(1R)-1-(2-bromophenyl)ethoxy]methyl]oxirane (1.06 g) obtained in Example 1, Step 1, tri-potassium phosphate (1.32 g), [bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (170 mg) and the mixture was heated under reflux for 7 hr. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1) to give the title compound (621 mg).

1. temperaturecooling
2. temperaturethe mixture was heated
3. temperatureunder reflux for 7 hr
4. temperatureThe reaction mixture was cooled to room temperature
5. extractionthe mixture was extracted with ethyl acetate
6. washThe organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1)