反应详情

A solution of 1.76 g (10 mmol) 8-methoxy tetralone, 2.66 g (20 mmol) N,N-bis(-2methoxyethyl)amine, and 25 mg p-toluenesulfonic acid in toluene was heated to reflux under a N2 atmosphere. The flask was equipped with a Dean-Stark trap to collect H2O. TLC analysis was used to monitor the reaction. After 48 hours, the solvent was removed in vacuo. The crude ene-amine was hydrogenated using 450 mg 10% pd/C in 50 mL MeOH at 50 psi H2 for 24 hours. The reaction mixture was filtered over celite and the filtrate purified by liquid chromatography on 400 g of silica gel-60 (230-400 mesh), eluting with hexane/ethyl acetate/isopropanol (10:5:1). Fractions homogeneous by TLC were combined and concentrated in vacuo to give pure title compound as a yellow oil (2.3 g, 80%).

1. temperatureto reflux under a N2 atmosphere
2. customThe flask was equipped with a Dean-Stark trap
3. customto collect H2O
4. customthe reaction
5. customthe solvent was removed in vacuo
6. waitpd/C in 50 mL MeOH at 50 psi H2 for 24 hours
7. filtrationThe reaction mixture was filtered over celite
8. customthe filtrate purified by liquid chromatography on 400 g of silica gel-60 (230-400 mesh)
9. washeluting with hexane/ethyl acetate/isopropanol (10:5:1)
10. concentrationconcentrated in vacuo