Water → 4-Chloro-alpha-cyclopropyl-alpha-methylbenzenemethanol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

1.50 g (9.70 mmol) of 4-chloroacetophenone were dissolved in 8 ml of diethyl ether at 0° C., and 38.8 ml (19.41 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were slowly added dropwise. Stirring at 0° C. for 1 h was followed by warming to RT, addition of water and acetonitrile to the reaction solution, and filtration of the mixture 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, and the solvents were removed in vacuo. The crude product was purified twice 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. 1.37 g (72% of theory) of the title compound were obtained.

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