反应详情

To a solution of the compound (5) (29.0 g, 45.0 mmol) in anhydrous tetrahydrofuran (THF, 150 ml), added was a solution of 0.5 M 9-borabicyclo[3,3,1]nonane (9-BBN) in tetrahydrofuran (180 ml, 90.0 mmol) at 0° C. in an argon atmosphere. After a lapse of 1 hour, the reaction liquid was returned to room temperature, and continuously stirred for 10 hours. The reaction liquid was cooled again to 0° C., to which water (20 ml) was added firstly, and then 3 M sodium hydroxide solution (70 ml) and 35% hydrogen peroxide solution (70 ml) were added sequentially. After a lapse of 1 hour, the reaction liquid was returned to room temperature, and stirred for 12 hours. After the sufficient progress of the reaction was confirmed, the solution was extracted with ethyl acetate (3×100 ml), the organic layers were combined and washed with saturated saline (2×100 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified with silica gel chromatography (hexane-ethyl acetate, 3:2→1:1→2:3) to obtain the title compound (6) in the form of a colorless oily substance {28.2 g (42.5 mmol), 94.4%}.

1. customat 0° C.
2. customAfter a lapse of 1 hour, the reaction liquid
3. customwas returned to room temperature
4. customThe reaction liquid
5. additionwas added firstly
6. customAfter a lapse of 1 hour, the reaction liquid
7. customwas returned to room temperature
8. stirringstirred for 12 hours
9. extractionthe solution was extracted with ethyl acetate (3×100 ml)
10. washwashed with saturated saline (2×100 ml)
11. dry with materialdried with sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customThe obtained residue was purified with silica gel chromatography (hexane-ethyl acetate, 3:2→1:1→2:3)