1: 1.) n-BuLi / 1.) THF, - 10 deg C, 2.) THF, RT 2: 1.2 N methanolic HCl 3: 57 percent / 5 h / 90 - 100 °C 4: 30 percent / H2, PtO2 / ethyl acetate / 760 Torr / Ambient temperature View Scheme

Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, - 10 deg C, 2.) THF, RT2: 1.2 N methanolic HCl  

Multi-step reaction with 4 steps 1: 1.) n-BuLi / 1.) THF, - 10 deg C, 2.) THF, RT2: 1.2 N methanolic HCl3: 57 percent / 5 h / 90 - 100 °C4: 12 percent / H2, PtO2 / ethyl acetate / 760 Torr / Ambient temperature  

Multi-step reaction with 4 steps 1: 1.) n-BuLi / 1.) THF, - 10 deg C, 2.) THF, RT2: 1.2 N methanolic HCl3: 57 percent / 5 h / 90 - 100 °C4: 19 percent / H2, PtO2 / ethyl acetate / 760 Torr / Ambient temperature  

Multi-step reaction with 3 steps 1: 1.) n-BuLi / 1.) THF, - 10 deg C, 2.) THF, RT2: 1.2 N methanolic HCl3: 57 percent / 5 h / 90 - 100 °C