tin(IV) chloride in dichloromethane 2 h; Heating;

PPA T=60 - 70°C; 4.5 h;

1: 72 percent / NaBH4 / ethanol / 2.5 h / Ambient temperature 2: cation exchange resin (Amberlyst-15) / benzene / 1.5 h / Heating 3: 100 percent / H2 / 5percent Pd/C / ethanol / 3 h / 2585.7 Torr View Scheme

1: 72 percent / NaBH4 / ethanol / 2.5 h / Ambient temperature 2: cation exchange resin (Amberlyst-15) / benzene / 1.5 h / Heating 3: 100 percent / H2 / 5percent Pd/C / ethanol / 3 h / 2585.7 Torr 4: 70 percent / SnCl4 / CH2Cl2 / 3 h / Heating View Scheme

1: 72 percent / NaBH4 / ethanol / 2.5 h / Ambient temperature 2: cation exchange resin (Amberlyst-15) / benzene / 1.5 h / Heating 3: 100 percent / H2 / 5percent Pd/C / ethanol / 3 h / 2585.7 Torr 4: 70 percent / SnCl4 / CH2Cl2 / 3 h / Heating 5: 66 percent / CH3COONH4 / 2.5 h / Heating View Scheme

potassium hydride 1.) tetrahydrofurane, room temp.; 2.) tetrahydrofurane, 10 min (N2), 30 min (air); Yield given. Multistep reaction;