Multi-step reaction with 7 steps 1: 1.) ethylmagnesium bromide, copper(I) bromide / 1.) THF, -78 -> 25 deg C, 2.) -78 -> 25 deg C2: H2 / Lindlar catalyst / hexane / 25 °C3: KF / dimethylformamide / 25 °C4: 90 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 12 h / 25 °C5: 60 percent / H2 / Lindlar catalyst / hexane / 25 °C6: 75 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C7: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C  

Multi-step reaction with 2 steps 1: 1a.) ethylmagnesium bromide, 1b.) cuprous chloride / 1a.) THF, reflux, 6 h, 1b.) 0 deg C, 15 min, 3.) reflux, 9 h2: 66 percent / p-TsOH / methanol / 4 h / Heating  

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  

Multi-step reaction with 3 steps 1.1: EtMgBr / tetrahydrofuran / 2 h / 20 °C1.2: cuprous cyanide / hexamethylphosphoric acid triamide; tetrahydrofuran / 50 °C2.1: conc. H2SO4 / CCl4 / Heating3.1: LiAlH4 / tetrahydrofuran