1: With lithium aluminium tetrahydride in tetrahydrofuran 2 h; Heating / reflux; 2: With water in tetrahydrofuran T=20°C;

toluene-4-sulfonic acid in methanol T=60°C; 0.5 h;

nickel; hydrazine hydrate in tetrahydrofuran; methanol T=20°C; 6 h;

1: 79 percent / pyridinium p-toluene sulfonate / CH2Cl2 / 3 h / 20 °C 2: dimethylformamide / 4 h / 130 °C 3: 48 percent / hydrazine hydrate; Raney nickel / tetrahydrofuran; methanol / 6 h / 20 °C 4: 100 percent / p-toluenesulfonic acid monohydrate / methanol / 0.5 h / 60 °C View Scheme

1: chlorotrimethylsilane; benzyltriethylammonium borohydride / CH2Cl2 / 24 h / 20 °C 2: 79 percent / pyridinium p-toluene sulfonate / CH2Cl2 / 3 h / 20 °C 3: dimethylformamide / 4 h / 130 °C 4: 48 percent / hydrazine hydrate; Raney nickel / tetrahydrofuran; methanol / 6 h / 20 °C 5: 100 percent / p-toluenesulfonic acid monohydrate / methanol / 0.5 h / 60 °C View Scheme

1: 2.) titanium(III) chloride / 1.) DMF, reflux, 13.5 h; 2.) water, MeOH, 7 min 2: 90.9 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: dimethylformamide / 4 h / 130 °C 2: 39 percent / hydrazine hydrate; Raney nickel / tetrahydrofuran; methanol / 6 h / 20 °C View Scheme

1: dimethylformamide / 4 h / 130 °C 2: 48 percent / hydrazine hydrate; Raney nickel / tetrahydrofuran; methanol / 6 h / 20 °C 3: 100 percent / p-toluenesulfonic acid monohydrate / methanol / 0.5 h / 60 °C View Scheme

lithium aluminium tetrahydride

pyridinium chlorochromate in dichloromethane T=20°C; 1.5 h;