sodium hydrogencarbonate in dichloromethane; water T=0 - 20°C; 1.5 h;

ammonium hydroxide in ethanol 4 h; Ambient temperature;

1: aq. NaOH / 24 h / 40 - 45 °C 2: 61.50 g / ethyl chloroformate / H2O / 0.67 h / 35 - 40 °C View Scheme

1: 1.) sodium hydride / 1.) THF, RT, 1 h, 2.) THF, RT, 1 h 2: 70 percent / potassium bicarbonate / dimethylformamide / 3 h / Ambient temperature View Scheme

1: 1.) sodium hydride / 1.) THF, RT, 1 h, 2.) THF, RT, 1 h 2: dimethylformamide / 2 h / Ambient temperature 3: diphenyl ether / 0.2 h / 250 °C 4: 84 percent / trifluoromethanesulfonic acid, trifluoroacetic acid, anisole / 2 h / Ambient temperature 5: 1.) potassium bicarbonate / 1.) DMF, 80 deg, 12 h, 2.) conc. sulfuric acid, 90 deg, 20 min. 6: 73 percent / sodium hydroxide, water / ethanol / 2 h / Heating 7: 41 percent / pyridine / 55 h / Heating View Scheme

1: 1.) sodium hydride / 1.) THF, RT, 1 h, 2.) THF, RT, 1 h 2: dimethylformamide / 2 h / Ambient temperature 3: diphenyl ether / 0.2 h / 250 °C 4: 84 percent / trifluoromethanesulfonic acid, trifluoroacetic acid, anisole / 2 h / Ambient temperature 5: 1.) potassium bicarbonate / 1.) DMF, 80 deg, 12 h, 2.) conc. sulfuric acid, 90 deg, 20 min. 6: 73 percent / sodium hydroxide, water / ethanol / 2 h / Heating 7: 52 percent / pyridine / 75 h / Heating View Scheme

1: 1.) sodium hydride / 1.) THF, RT, 1 h, 2.) THF, RT, 1 h 2: dimethylformamide / 2 h / Ambient temperature 3: diphenyl ether / 0.2 h / 250 °C 4: 84 percent / trifluoromethanesulfonic acid, trifluoroacetic acid, anisole / 2 h / Ambient temperature 5: 1.) sodium / 1.) ethanol, 0 de C,1,5 h, 2.) ethanol, RT, 3,5 h 6: 72 percent / conc. sulfuric acid / 1 h / 0 °C 7: 88 percent / sodium hydroxide, water / ethanol / 2 h / Heating 8: 13 percent / pyridine / 55 h / Heating View Scheme

1: 1.) sodium hydride / 1.) THF, RT, 1 h, 2.) THF, RT, 1 h 2: 70 percent / potassium bicarbonate / dimethylformamide / 3 h / Ambient temperature 3: 33 percent / polyphosphoric acid / 2 h / 120 °C View Scheme

1: 1.) sodium hydride / 1.) THF, RT, 1 h, 2.) THF, RT, 1 h 2: dimethylformamide / 2 h / Ambient temperature 3: diphenyl ether / 0.2 h / 250 °C 4: 84 percent / trifluoromethanesulfonic acid, trifluoroacetic acid, anisole / 2 h / Ambient temperature 5: 1.) sodium / 1.) ethanol, 0 de C,1,5 h, 2.) ethanol, RT, 3,5 h 6: 72 percent / conc. sulfuric acid / 1 h / 0 °C 7: 88 percent / sodium hydroxide, water / ethanol / 2 h / Heating 8: 34 percent / pyridine / 75 h / Heating View Scheme