反应详情

温度

110 °C

To a flask charged with 1.55 g of (PPh3)2PdCl2 and 5.0 g of 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one was added 25 mL of DMF. Then 9.58 g of Tributyl-(1-ethoxy-vinyl)-stannane was added and the reaction mixture was heated to 110° C. and stirred until completion of the reaction. The reaction mixture was filtered over celite and diluted with diethyl ether. After washing with saturdated ammonium carbonate, water and brine, the solutin was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting mixture dissolved in THF and treated with 3.0 M aqueous HCl to effect hydrolysis. The mixture was then partitioned between water and diethyl ether. The organic phase was washed sequentially with saturated sodium bicarbonate, water, and brine and then dried over sodium sulfate. After filtration, the solution was concentrated and purified by flash chromatography to afford the 3.28 g of 6-Acetyl-3,4-dihydro-2H-isoquinolin-1-one.

1. filtrationThe reaction mixture was filtered over celite
2. additiondiluted with diethyl ether
3. washAfter washing with saturdated ammonium carbonate, water and brine
4. dry with materialthe solutin was dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. dissolutionThe resulting mixture dissolved in THF
8. additiontreated with 3.0 M aqueous HCl
9. customhydrolysis
10. customThe mixture was then partitioned between water and diethyl ether
11. washThe organic phase was washed sequentially with saturated sodium bicarbonate, water, and brine
12. dry with materialdried over sodium sulfate
13. filtrationAfter filtration
14. concentrationthe solution was concentrated
15. custompurified by flash chromatography