1: KF / dimethylformamide / 25 °C 2: 90 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 12 h / 25 °C 3: 60 percent / H2 / Lindlar catalyst / hexane / 25 °C 4: 75 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 5: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

Multi-step reaction with 5 steps 1: KF / dimethylformamide / 25 °C2: 90 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 12 h / 25 °C3: 60 percent / H2 / Lindlar catalyst / hexane / 25 °C4: 75 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C5: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C  

Multi-step reaction with 2 steps 1: 1.) ethylmagnesium bromide, copper(I) bromide / 1.) THF, -78 -> 25 deg C, 2.) -78 -> 25 deg C2: H2 / Lindlar catalyst / hexane / 25 °C