反应详情

温度

50 °C

27.9 g of crude 4-(4-tert-butyl-phenyl)-2-[(1-methylcyclohexyl)methyl]-indan-1-one (˜83% purity), 2.82 g (74.5 mmol) of NaBH4 and 70.5 ml of toluene are charged in a flask equipped with reflux condenser, dropping funnel and magnetic stirring bar. The mixture is warmed to 50° C. and 14 ml of methanol are slowly added with stirring and stirring is continued for 2.5 h to ensure a complete reaction. Excess NaBH4 is carefully hydrolyzed with approx. 40 ml of 2n H2SO4. The organic phase is separated and the water phase is washed with another 35 ml of toluene. The combined organic phases are twice extracted with 2n H2SO4 and dried over anhydrous MgSO4. Most of the solvent is removed in a vacuum and replaced by fresh toluene up to a total volume of 100 ml and 0.3 g of p-toluenesulfonic acid are added. The reaction flask is fitted with a water separator and the reaction mixture is heated to reflux for 1.5 h. The conversion can be monitored by TLC. Once the dehydration is complete, the solution is washed with a saturated NaHCO3 solution and dried over anhydrous MgSO4. The solvent is thoroughly removed in a vacuum and 25.85 g of a brown oil is obtained. Purification of the indene is carried out via a column chromatography. Yield: 18.85 g (˜85%) of 7-(4-tert-Butyl-phenyl)-2-[(1-methylcyclohexyl)methyl]-1H-indene.

1. customequipped
2. temperaturewith reflux condenser
3. stirringstirring
4. customa complete reaction
5. customThe organic phase is separated
6. washthe water phase is washed with another 35 ml of toluene
7. extractionThe combined organic phases are twice extracted with 2n H2SO4
8. dry with materialdried over anhydrous MgSO4
9. customMost of the solvent is removed in a vacuum
10. additionare added
11. customThe reaction flask is fitted with a water separator
12. temperaturethe reaction mixture is heated
13. temperatureto reflux for 1.5 h
14. washthe solution is washed with a saturated NaHCO3 solution
15. dry with materialdried over anhydrous MgSO4
16. customThe solvent is thoroughly removed in a vacuum