lithium; ethylenediamine in tetrahydrofuran T=25°C; 2 h; continuous flow of ethyne;

in dimethyl sulfoxide T=20°C; 21 h;

lithium in tetrahydrofuran; ethylenediamine

sodium in tetrahydrofuran; ammonia T=-4°C; 1 h;

1: 80 percent / NaH, MeOH / tetrahydrofuran; hexane / 1 h / Heating 2: 1.) NaH, 2.) n-BuLi 3: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 4: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 5: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 6: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 7: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 8: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 9: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 10: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 11: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 12: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

1: 1.) NaH, 2.) n-BuLi 2: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 3: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 4: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 5: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 6: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 7: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 8: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 9: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 10: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 11: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 2: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

1: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 2: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 3: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 4: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

1: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 2: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 3: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 4: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 5: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 6: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 7: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 8: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 9: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

1: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 2: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 3: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme