sodium hydroxide in methanol T=60°C; 2 h;

1: 1.) aq. H2SO4, NaN2, 2.) aq H2SO4 / 2.) reflux, 30 min 2: 82.4 percent / AcCl / 18 h / Ambient temperature 3: 81 percent / NaH / tetrahydrofuran / 8 h / Heating 4: 86 percent / H2 / 10percent Pd/C / methanol / 18 h / 1810.02 Torr 5: 87 percent / Et3N / tetrahydrofuran / 1.5 h 6: 91 percent / aq. NaOH / methanol / 2 h / 60 °C View Scheme

1: 80 percent / 1.) aq. NH3, 2.) H2S 2: 1.) aq. H2SO4, NaN2, 2.) aq H2SO4 / 2.) reflux, 30 min 3: 82.4 percent / AcCl / 18 h / Ambient temperature 4: 81 percent / NaH / tetrahydrofuran / 8 h / Heating 5: 86 percent / H2 / 10percent Pd/C / methanol / 18 h / 1810.02 Torr 6: 87 percent / Et3N / tetrahydrofuran / 1.5 h 7: 91 percent / aq. NaOH / methanol / 2 h / 60 °C View Scheme

1: 81 percent / NaH / tetrahydrofuran / 8 h / Heating 2: 86 percent / H2 / 10percent Pd/C / methanol / 18 h / 1810.02 Torr 3: 87 percent / Et3N / tetrahydrofuran / 1.5 h 4: 91 percent / aq. NaOH / methanol / 2 h / 60 °C View Scheme

1: 82.4 percent / AcCl / 18 h / Ambient temperature 2: 81 percent / NaH / tetrahydrofuran / 8 h / Heating 3: 86 percent / H2 / 10percent Pd/C / methanol / 18 h / 1810.02 Torr 4: 87 percent / Et3N / tetrahydrofuran / 1.5 h 5: 91 percent / aq. NaOH / methanol / 2 h / 60 °C View Scheme

1: 86 percent / H2 / 10percent Pd/C / methanol / 18 h / 1810.02 Torr 2: 87 percent / Et3N / tetrahydrofuran / 1.5 h 3: 91 percent / aq. NaOH / methanol / 2 h / 60 °C View Scheme

1: 87 percent / Et3N / tetrahydrofuran / 1.5 h 2: 91 percent / aq. NaOH / methanol / 2 h / 60 °C View Scheme