1: 1.) lithium diisopropylamide (LDA) / 1.) THF, -70 deg C, 15 min, 2.) THF, -70 deg C, 1.5 h 2: 91 percent / H2 / 5percent Pd/C / ethanol / 1 h / Ambient temperature 3: DIBAL / toluene / 0.5 h / -40 °C 4: SOCl2 / 0.5 h / Ambient temperature 5: dimethylsulfoxide / 3 h / 60 °C 6: concd. HCl / 72 h / 60 - 70 °C View Scheme

1: 91 percent / H2 / 5percent Pd/C / ethanol / 1 h / Ambient temperature 2: DIBAL / toluene / 0.5 h / -40 °C 3: SOCl2 / 0.5 h / Ambient temperature 4: dimethylsulfoxide / 3 h / 60 °C 5: concd. HCl / 72 h / 60 - 70 °C View Scheme

hydrogenchloride T=60 - 70°C; 72 h;

1: SOCl2 / 0.5 h / Ambient temperature 2: dimethylsulfoxide / 3 h / 60 °C 3: concd. HCl / 72 h / 60 - 70 °C View Scheme

1: dimethylsulfoxide / 3 h / 60 °C 2: concd. HCl / 72 h / 60 - 70 °C View Scheme

1: DIBAL / toluene / 0.5 h / -40 °C 2: SOCl2 / 0.5 h / Ambient temperature 3: dimethylsulfoxide / 3 h / 60 °C 4: concd. HCl / 72 h / 60 - 70 °C View Scheme