1: {1-[chloro(p-tolylsulfinyl)methyl]cyclopentadecyl}acetonitrile With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 0.5 h; 2: lithium α-carbanion of propionitrile in tetrahydrofuran T=-78 - 20°C; 2.5 h;

1: {1-[chloro(p-tolylsulfinyl)methyl]cyclopentadecyl}acetonitrile With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 0.5 h; 2: anhydrous propionitrile With n-butyllithium in tetrahydrofuran T=-78 - 20°C; 2.5 h;

1.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C 1.2: 97 percent / tetrahydrofuran / 0.17 h / -78 °C 2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C 2.2: 80 percent / n-butyllithium / tetrahydrofuran / 2.5 h / -78 - 20 °C View Scheme