hydrogen; palladium on activated charcoal in acetic acid P=3750.3 Torr; 10 h; Ambient temperature;

sodium cyanoborohydride in dichloromethane; acetic acid; acetonitrile

potassium tert-butylate in dimethyl sulfoxide T=50°C; 2 h;

1: 81 percent / thionyl chloride / CH2Cl2 / 1 h / Heating 2: triethylamine / CH2Cl2 / 1 h / Ambient temperature 3: 75 percent / glacial acetic acid, conc. HCl / 17 h / Ambient temperature 4: 1.) potassium tert-butoxide / 1.) DMSO, RT, 30 min, 2.) RT, 30 min 5: 2 h / 90 - 95 °C 6: H2 / Pd/C / acetic acid / 10 h / 3750.3 Torr / Ambient temperature View Scheme

1: 1.) potassium tert-butoxide / 1.) DMSO, RT, 30 min, 2.) RT, 30 min 2: 2 h / 90 - 95 °C 3: H2 / Pd/C / acetic acid / 10 h / 3750.3 Torr / Ambient temperature View Scheme

1: 2 h / 90 - 95 °C 2: H2 / Pd/C / acetic acid / 10 h / 3750.3 Torr / Ambient temperature View Scheme

1: 75 percent / glacial acetic acid, conc. HCl / 17 h / Ambient temperature 2: 1.) potassium tert-butoxide / 1.) DMSO, RT, 30 min, 2.) RT, 30 min 3: 2 h / 90 - 95 °C 4: H2 / Pd/C / acetic acid / 10 h / 3750.3 Torr / Ambient temperature View Scheme

1: triethylamine / CH2Cl2 / 1 h / Ambient temperature 2: 75 percent / glacial acetic acid, conc. HCl / 17 h / Ambient temperature 3: 1.) potassium tert-butoxide / 1.) DMSO, RT, 30 min, 2.) RT, 30 min 4: 2 h / 90 - 95 °C 5: H2 / Pd/C / acetic acid / 10 h / 3750.3 Torr / Ambient temperature View Scheme

1: 40 percent / t-BuOK / dimethylsulfoxide / 2 h / 50 °C View Scheme

1: 89 percent / toluene / 2 h / Heating 2: 76 percent / aq. KOH / acetonitrile; H2O / 3 h / 20 °C 3: 71 percent / aq. silver nitrate / acetonitrile; H2O / 16 h / 20 °C 4: 95 percent / Na; liq. NH3 / tetrahydrofuran / 0.5 h / -78 °C 5: 98 percent / Me3SiCl; NaI / acetonitrile / 24 h / 20 °C 6: 40 percent / t-BuOK / dimethylsulfoxide / 2 h / 50 °C View Scheme