反应详情

温度

80 °C

To a mixture of (1R,2S,3S,4R,55)-1-(acetoxymethyl)-5-(3-(bromomethyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (1.0 g, 1.77 mmol, Intermediate 2), 1-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)phenyl)ethanone (899.0 mg, 2.66 mmol), Pd (dppf) Cl2 (72 mg, 0.09 mmol) and sodium carbonate (563.0 mg, 5.31 mmol) under nitrogen atmosphere, was added DMF and H2O (9 mL, 1:1). The reaction mixture was heated at 80° C. for 1 h. After the completion of the reaction, as confirmed by TLC, the solution was cooled to r.t. and filtered through celite. The solvent was evaporated in vacuo and the crude compound was diluted with ethyl acetate (200 mL). The organic layer was washed with water (3×30 mL), separated, dried over Na2SO4 and concentrated in vacuo to afford crude compound which was purified by column chromatography (silica gel, 1:4 EtOAc:Pet ether) to afford the title compound (450 mg, 36.6%) as a white solid.

1. customAfter the completion of the reaction
2. temperaturethe solution was cooled to r.t.
3. filtrationfiltered through celite
4. customThe solvent was evaporated in vacuo
5. additionthe crude compound was diluted with ethyl acetate (200 mL)
6. washThe organic layer was washed with water (3×30 mL)
7. customseparated
8. dry with materialdried over Na2SO4
9. concentrationconcentrated in vacuo
10. customto afford crude compound which
11. customwas purified by column chromatography (silica gel, 1:4 EtOAc:Pet ether)