Iodine → 1-(1-Benzothiophen-5-yl)-1-cyclopropylethanol

Participants

Reaction Steps

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.

Provenance & Evidence