sodium tetrahydroborate in water T=50 - 60°C; chemoselective reaction;

1: pyridine With (2,2,6,6-tetramethylpiperidinyl)MgCl*LiCl; boron trifluoride diethyl etherate in tetrahydrofuran T=-40°C; Inert atmosphere; 2: 4-chlorobenzaldehyde in tetrahydrofuran T=-40 - 25°C; Inert atmosphere; 3: 2-dimethylamino-1-chloro-ethane hydrochloride With sodium hydride; sodium iodide in tetrahydrofuran; mineral oil T=25 - 50°C; Neat (no solvent)Inert atmosphere; regioselective reaction;

xylene

sodium hydroxide in water Heating;