[CH3:1][N:2]([CH:4]([CH:7]1CCC2(OCCO2)C[CH2:8]1)[C:5]#N)[CH3:3].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([Mg]Br)=[CH:20][CH:19]=1.[Cl-].[NH4+].[OH2:28].[CH3:29][CH2:30][O:31][CH2:32][CH3:33]>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:1][N:2]([CH:4]2[CH2:7][CH2:8][C:30]3([O:28][CH2:33][CH2:32][O:31]3)[CH2:29][CH2:5]2)[CH3:3])=[CH:20][CH:19]=1A solution of the aminonitrile 6 (22.43 g, 100 mmole) in absolute ether (100 ml) was added to a 1M solution of 4-chlorophenyl magnesium bromide in ether (200 ml, 200 mmole) under argon and while cooling with ice, and stirred for 20 hours at RT. To work up the reaction mixture, saturated ammonium chloride solution (100 ml) and water (100 ml) were added while cooling with ice, and the mixture was extracted with diethyl ether (3×100 ml). The organic phase was washed with water and saturated sodium chloride solution, dried, and concentrated by evaporation.
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