反应详情

0.60 g (24.64 mmol) of magnesium turnings were dried by heating under argon and, after cooling to RT, 30 ml of tetrahydrofuran were added. 5.00 g (23.46 mmol) of 5-bromo-1-benzothiophene in 30 ml of tetrahydrofuran, and traces of iodine, were added to the mixture, which was stirred at RT for 30 min. Addition of 2.17 g (25.81 mmol) of acetylcyclopropane in 30 ml of tetrahydrofuran was followed by stirring for 2 h. The reaction solution was mixed with water and acetonitrile, and the mixture was filtered through kieselguhr. The organic solvents were removed in a rotary evaporator, and the aqueous phase was extracted twice with diethyl ether. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered, and the solvents were removed in vacuo. The crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). The acetonitrile was removed from the combined product phases in a rotary evaporator, and the aqueous phase was extracted twice with diethyl ether. The combined organic phases were again washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered, and the solvents were removed in vacuo. 2.39 g (46% of theory) of the title compound were obtained.

1. temperatureby heating under argon
2. stirringby stirring for 2 h
3. filtrationthe mixture was filtered through kieselguhr
4. customThe organic solvents were removed in a rotary evaporator
5. extractionthe aqueous phase was extracted twice with diethyl ether
6. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customthe solvents were removed in vacuo
10. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)
11. customThe acetonitrile was removed from the combined product phases in a rotary evaporator
12. extractionthe aqueous phase was extracted twice with diethyl ether
13. washThe combined organic phases were again washed with saturated aqueous sodium chloride solution
14. dry with materialdried over sodium sulfate
15. filtrationfiltered
16. customthe solvents were removed in vacuo