Ammonium Chloride → HCID 59504645, compound

Participants

Reaction Conditions

Reaction Steps

Under inert conditions, 11 ml (21.8 mmol) of a 2 M solution of isopropylmagnesium chloride in diethyl ether were added dropwise at −40° C. to a solution of 5.0 g (21.8 mmol) of 4-iodobenzonitrile in 100 ml of anhydrous THF. After the mixture had been stirred at the same temperature for 1.5 h, it was cooled down to −78° C. and, with the aid of a cannula, was slowly added to a solution, likewise cooled to −78° C., of 2.95 g (32.7 mmol, 80% in dichloromethane) of 3-oxooxetane [G. Wuitschik et al., Angew. Chem. Int. Ed. Engl. 2006, 45 (46), 7736-7739] in 100 ml of anhydrous THF. After the addition had ended, the reaction mixture was stirred first at −78° C. for 10 min, then at 0° C. for 2 h and finally at RT for 30 min. Then a few ml of saturated aqueous ammonium chloride solution were added. Subsequently, the solvent was substantially removed on a rotary evaporator. The residue obtained was diluted with 200 ml of water and extracted three times with approx. 200 ml each time of ethyl acetate. The combined organic extracts were washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate, the mixture was filtered and the solvent was removed on a rotary evaporator. The resulting crude product was purified by crystallization from 10:1 cyclohexane/ethyl acetate. 2.42 g (63% of theory) of the title compound were obtained.

Provenance & Evidence