18637-00-8

21.4 g (400 mmol) of ammonium chloride was suspended in 375 ml of toluene, and the suspension was cooled to 0°C. 200 ml of 2M trimethylaluminum in hexane was added dropwise, and the mixture was stirred at room temperature until gas escape stopped. 29.44 g (200 mmol) of 2-ethoxybenzyl nitrile was added, and the reaction mixture was stirred overnight at 80°C (bath). The cooled reaction mixture was added under ice-cooling to a suspension of 100 g silica gel and 950 ml chloroform, and the mixture was stirred at room temperature for 30 minutes. The mixture was filtered, and the residue was washed with the same amount of methanol. The mother liquor was evaporated, and the resulting residue was stirred together with a mixture of dichloromethane and methanol (9:1). The solid was filtered, and the mother liquor was evaporated again. 30.4 g (76%) of colorless solid was obtained.