反应详情

4-(4-Chloro-1,2-diphenyl-but-1-enyl)phenol (0.23 g, 0.689 mmol) was dissolved in tetrahydrofuran (3 ml) under nitrogen atmosphere. Sodium hydride (0.025 g, 1.03 mmol) was added to the solution and the mixture was stirred at room temperature for an hour. 2-(2-iodo-ethoxy)-tetrahydropyran (0.3 g, 1.17 mmol) was added and the mixture was refluxed for 2 hours. Additional portions of 2-(2-iodo-ethoxy)-tetrahydro-pyran (0.5 g, 2 mmol) were added to the mixture during seven hours. After cooling and adding water, THF was evaporated and the mixture was extracted three times with ethyl acetate. The organic phase was washed with 2 N aqueous sodium hydroxide and water, dried with sodium sulphate and evaporated to dryness. The residue (which is Compound (IV) where Pr is tetrahydropyranyl) was dissolved in ethanol and acidified with 2 N aqueous hydrogen chloride solution. The mixture was stirred at room temperature over night, evaporated and extracted with dichloromethane. After washing with water the organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography with dichloromethane/methanol 9.5/0.5 as eluent. Yield 0.17 g, 59%.

1. temperaturethe mixture was refluxed for 2 hours
2. temperatureAfter cooling
3. customwas evaporated
4. extractionthe mixture was extracted three times with ethyl acetate
5. washThe organic phase was washed with 2 N aqueous sodium hydroxide and water
6. dry with materialdried with sodium sulphate
7. customevaporated to dryness
8. dissolutionThe residue (which is Compound (IV) where Pr is tetrahydropyranyl) was dissolved in ethanol
9. stirringThe mixture was stirred at room temperature over night
10. customevaporated
11. extractionextracted with dichloromethane
12. washAfter washing with water the organic phase
13. dry with materialwas dried (Na2SO4)
14. customevaporated
15. customThe residue was purified by flash chromatography with dichloromethane/methanol 9.5/0.5 as eluent