1: 100 percent / potassium hydroxide / dimethylsulfoxide / 4 h / 45 °C 2: 42 percent / methanol / 32 h / 100 °C View Scheme

potassium tert-butylate in N,N-dimethyl-formamide T=0°C; 0.5 h;

caesium carbonate; potassium iodide in acetone T=20°C; 14 h;

1: With sodium cyanoborohydride; acetic acid T=15 - 20°C; 1.5 h; 2: With sodium hydrogencarbonate in water; ethyl acetate

potassium carbonate in acetone T=20°C; 5 h;

1.1: 85 percent / imidazole / CH2Cl2 / 20 °C 2.1: 100 percent / tetrabutylammonium bromide; sodium hydroxide / CH2Cl2 / 18 h / 20 °C 3.1: 70 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 0.67 h / 0 °C 4.1: potassium carbonate / acetone / 0.25 h / 20 °C 4.2: 81 percent / acetone / 17 h / Heating 5.1: 82 percent / H2 / Pd/C / ethanol / 1 h View Scheme

1.1: 94 percent / K2CO3 / acetone / 72 h / Heating 2.1: NaH / dimethylformamide / 0.08 h / 0 °C 2.2: 80 percent / dimethylformamide / 0.5 h / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 3.2: 89 percent / hexane; tetrahydrofuran / 12.5 h / -78 - 20 °C View Scheme

1.1: 94 percent / K2CO3 / acetone / 72 h / Heating 2.1: NaH / dimethylformamide / 0.08 h / 0 °C 2.2: 80 percent / dimethylformamide / 0.5 h / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 3.2: 89 percent / hexane; tetrahydrofuran / 12.5 h / -78 - 20 °C 4.1: 62 percent / lithium aluminum hydride / tetrahydrofuran / 12 h / Heating 5.1: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 6.1: NaH / dimethylformamide / 0.08 h / 0 °C 6.2: 83 percent / dimethylformamide / 2 h 7.1: 68 percent / H2 / Pd/C / methanol / 2 h / 2068.59 Torr 8.1: NaH / dimethylformamide / 0.08 h / 20 °C 8.2: 87 percent / dimethylformamide / 0.5 h 9.1: CH2Cl2 / 2 h / 20 °C 10.1: 0.505 g / NH3 / CH2Cl2 / 0.17 h / 20 °C View Scheme

1: Cs2CO3 / acetone / Heating 2: POCl3 / 0 - 60 °C View Scheme

1.1: 82 percent / triphenylphosphine; DEAD / tetrahydrofuran / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran 2.2: 86 percent / tetrahydrofuran 3.1: 96 percent / NaN3 / dimethylformamide 4.1: 80 percent / PPh3; water View Scheme