1: 22 percent / 1M sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C 2: 99 percent / H2 / Lindlar's catalyst / benzene / 0.33 h / 760 Torr 3: 53 percent / lithium diisopropylaminde / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -108 °C 4: 70 percent Turnov. / 1M triethylaluminum, tetrakis(triphenylphosphine)palladium(0) / hexane; 1,2-dichloro-ethane / 10.5 h / 20 °C 5: 96 percent / KOH / H2O; methanol / 4 h / Heating 6: triethylamine / CH2Cl2 / 0.5 h / -23 °C 7: 100 percent / NaCN / dimethylsulfoxide / 5 h / 20 °C 8: KOH / ethanol / 5 h / Heating View Scheme

Multi-step reaction with 2 steps 1: 22 percent / 1M sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C2: 99 percent / H2 / Lindlar's catalyst / benzene / 0.33 h / 760 Torr  

Multi-step reaction with 3 steps 1: 22 percent / 1M sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C2: 99 percent / H2 / Lindlar's catalyst / benzene / 0.33 h / 760 Torr3: lithium diisopropylaminde / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -108 °C