反应详情

5,6-Dimethoxy-3-phenyl-1,2,3,4-tetrahydro-1-naphthalenone (14.6 g, 51.7 mmol), from Example 1, 24 mL of acetonitrile, 10.3 g (104 mmol) of trimethylsilylcyanide, commercially available from Aldrich Chemical Company, and 100 mg of aluminum chloride were mixed together and heated at reflux temperature for 2.5 h. The reaction mixture was cooled and concentrated. The residue was dissolved in diethyl ether and added dropwise to a solution of 4.3 g (113 mmol) of lithium aluminum hydride in 101 mL of diethyl ether. After the reaction mixture was heated at reflux temperature for 2.5 h, 4.3 mL of water was added dropwise, followed by 4.3 mL of 15% aqueous sodium hydroxide solution, followed by 13 mL of water. The reaction mixture was stirred until a qranular precipitate formed. The solid was filtered and washed with 3×80 mL of methylene chloride. The filtrate was concentrated and the resultant solid was triturated with ethyl acetate/hexane to give 11.9 g (73% yield) of the title compound, m.p. 175°-176° C. 1H NMR (d6DMSO) delta 2.03 (t, 1H), 2.28 (dt, 1H), 2.65 (dd, 1H), 2.83 (dd, 1H), 2.95-3.1 (m, 2H), 3.28 (dd, 1H), 3.75 (s, 3H), 3.86 (s, 3H), 6.87 (d, 1H), 7.2-7.4 (m, 6H)

1. temperatureheated
2. temperatureat reflux temperature for 2.5 h
3. temperatureThe reaction mixture was cooled
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in diethyl ether
6. temperatureAfter the reaction mixture was heated
7. temperatureat reflux temperature for 2.5 h
8. customformed
9. filtrationThe solid was filtered
10. washwashed with 3×80 mL of methylene chloride
11. concentrationThe filtrate was concentrated
12. customthe resultant solid was triturated with ethyl acetate/hexane