1: NaNH2; diethyl ether 3: ZnCl2; concentrated aqueous HCl View Scheme

lithium aluminium tetrahydride

1: trichlorophosphate / 19 h / 20 °C 2: AlCl3, aluminium chloride / dichloromethane / 45 h / 40 °C 3: potassium phosphate; [RhCl(η2:η2-cycloocta-1,5-diene)]2; (Ra,R,R)-SIPHOS-PE / 1,2-dichloro-ethane / 18 h / 70 °C / |Inert atmosphere View Scheme

1: 1.) POCl3 / 1.) 45 min, 2.) 25 deg C, 17 h 2: 85 percent / toluene / 18 h / Heating 3: 98 percent / H2 / 5percent Pd/C / methanol / 2327.2 Torr 4: NaH / 1,2-dimethoxy-ethane / 0.5 h / Heating 5: 20percent aq. HCl / aq. ethanol / 18 h / Heating View Scheme

1: 1.) POCl3 / 1.) 45 min, 2.) 25 deg C, 17 h 2: 85 percent / toluene / 18 h / Heating 3: 98 percent / H2 / 5percent Pd/C / methanol / 2327.2 Torr 4: NaH / 1,2-dimethoxy-ethane / 0.5 h / Heating 5: 20percent aq. HCl / aq. ethanol / 18 h / Heating 6: p-toluenesulfonic acid / benzene / Heating View Scheme

1: 1.) POCl3 / 1.) 45 min, 2.) 25 deg C, 17 h 2: 85 percent / toluene / 18 h / Heating 3: 98 percent / H2 / 5percent Pd/C / methanol / 2327.2 Torr 4: NaH / 1,2-dimethoxy-ethane / 0.5 h / Heating 5: 20percent aq. HCl / aq. ethanol / 18 h / Heating 6: p-toluenesulfonic acid / benzene / Heating 7: 1.) 80 deg C, 3 h, 2.) 130 deg C, 30 min View Scheme