1: 98 percent / K2CO3 / acetone / 16 h 2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 100 deg C, 3 d View Scheme

1: 98 percent / K2CO3 / acetone / 16 h 2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 100 deg C, 3 d View Scheme

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

1: 98 percent / H2 / 10percent Pd/C / methanol / 16 h / 2327.2 Torr 2: 76 percent / DIAD, PPh3 / tetrahydrofuran / 2 h / Ambient temperature View Scheme

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

hydrogen; palladium on activated charcoal in methanol P=2327.2 Torr; 16 h;