potassium carbonate in acetone T=50°C;

sodium ethanolate; sodium in ethanol; water

potassium carbonate in acetone 16 h;

sodium hydride 1.) DMF, 30 min, 2.) DMF, 100 deg C, 3 d; Yield given. Multistep reaction;

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 100 deg C, 3 d 2: 98 percent / H2 / 10percent Pd/C / methanol / 16 h / 2327.2 Torr 3: 76 percent / DIAD, PPh3 / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 100 deg C, 3 d 2: 98 percent / H2 / 10percent Pd/C / methanol / 16 h / 2327.2 Torr 3: 76 percent / DIAD, PPh3 / tetrahydrofuran / 2 h / Ambient temperature 4: 1.) BuLi, 2.) Cl3CCCl3 / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 10 min View Scheme

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 100 deg C, 3 d 2: 98 percent / H2 / 10percent Pd/C / methanol / 16 h / 2327.2 Torr View Scheme