toluene-4-sulfonic acid in N,N-dimethyl-formamide T=60°C; benzylidenation; P=20 Torr; 1.5 h;

1: 28 percent / N-bromosuccinimide / 3 h / 0 °C 2: methanol; sodium methoxide / 3 h / 20 °C 3: 4.5 g / H2 / Raney nickel / methanol / 24 h 4: 65 percent / p-toluenesulfonic acid / dimethylformamide / 3 h / 60 °C / 20 Torr 5: 100 percent / pyridine / CH2Cl2 / 0.5 h / -15 °C 6: 1.25 g / NaN3 / dimethylformamide / 5 h / 20 °C View Scheme

1: 4.5 g / H2 / Raney nickel / methanol / 24 h 2: 65 percent / p-toluenesulfonic acid / dimethylformamide / 3 h / 60 °C / 20 Torr 3: 100 percent / pyridine / CH2Cl2 / 0.5 h / -15 °C 4: 1.25 g / NaN3 / dimethylformamide / 5 h / 20 °C View Scheme

1: methanol; sodium methoxide / 3 h / 20 °C 2: 4.5 g / H2 / Raney nickel / methanol / 24 h 3: 65 percent / p-toluenesulfonic acid / dimethylformamide / 3 h / 60 °C / 20 Torr 4: 100 percent / pyridine / CH2Cl2 / 0.5 h / -15 °C 5: 1.25 g / NaN3 / dimethylformamide / 5 h / 20 °C View Scheme

1: 100 percent / pyridine / CH2Cl2 / 0.5 h / -15 °C 2: 1.25 g / NaN3 / dimethylformamide / 5 h / 20 °C View Scheme

1: 9.4 g / acetic acid; sodium azide / H2O / 18 h / 20 °C 2: 7.9 g / pyridine / CH2Cl2 / 24 h / 20 °C 3: 1.68 g / K10 Montmorillonite / benzene / 18 h / Heating 4: 112 mg / sodium methoxide; methanol / 18 h / 20 °C 5: 57 percent / p-TsOH / dimethylformamide / 1.5 h / 60 °C / 20 Torr View Scheme

1: 65 percent / p-toluenesulfonic acid / dimethylformamide / 3 h / 60 °C / 20 Torr 2: 100 percent / pyridine / CH2Cl2 / 0.5 h / -15 °C 3: 1.25 g / NaN3 / dimethylformamide / 5 h / 20 °C View Scheme

1: 1.68 g / K10 Montmorillonite / benzene / 18 h / Heating 2: 112 mg / sodium methoxide; methanol / 18 h / 20 °C 3: 57 percent / p-TsOH / dimethylformamide / 1.5 h / 60 °C / 20 Torr View Scheme