反应详情

To a stirring solution of 1-octene (0.148 g, 1.3 mmol, 1.4 eq) in tetrahydrofuran (2 ml) under argon at 0° C. was added 9-BBN in tetrahydrofuran (0.5M, 2.7 ml, 1.4 mmol, 1.5 eq). The reaction was allowed to warm to room temperature and stirred for 9 hours then 34 (0.504 g, 0.9 mmol) (produced as described in Example 2) in tetrahydrofuran (5 ml), 3M NaOH solution (1.1 ml) and dichloropalladium (dppf) (0.031 g, 0.04 mmol, 0.04 eq) were added and the reaction heated to reflux for 15 hours. The reaction was then quenched with water and diethyl ether. The organic layer was collected and the aqueous layer extracted with dichloromethane. The combined organic layers were washed with brine dried (MgSO4) and concentrated in vacuo to give a orange oil. Column chromatography (silica gel, DCM) yielded 39f (0.290 g, 59%) as a colourless oil.

1. temperaturethe reaction heated
2. temperatureto reflux for 15 hours
3. customThe reaction was then quenched with water and diethyl ether
4. customThe organic layer was collected
5. extractionthe aqueous layer extracted with dichloromethane
6. washThe combined organic layers were washed with brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo
9. customto give a orange oil