sodium hydride; sodium chloride 1.) DMF; 2.) H2O, DMSO, 170 deg C, 4h; Yield given. Multistep reaction;

1: NaH / tetrahydrofuran / 0.5 h / Ambient temperature 2: 92 percent / tetrahydrofuran / 0.5 h / Ambient temperature 3: 94 percent / 2,6-lutidine, LiI*2H2O / 1 h / 150 °C 4: 72 percent / m-chloroberbenzoic acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: NaH / tetrahydrofuran / 0.5 h / Ambient temperature 2: 92 percent / tetrahydrofuran / 0.5 h / Ambient temperature 3: 94 percent / 2,6-lutidine, LiI*2H2O / 1 h / 150 °C View Scheme

lithium diisopropyl amide in tetrahydrofuran T=-78°C; 0.5 h;

in tetrahydrofuran Heating;

1: NaH / tetrahydrofuran / 0.5 h / Ambient temperature 2: 95 percent / tetrahydrofuran / 0.5 h / Ambient temperature 3: 99 percent / 2,6-lutidine, LiI*2H2O / 1 h / 150 °C 4: 86 percent / m-chloroberbenzoic acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: NaH / tetrahydrofuran / 0.5 h / Ambient temperature 2: 92 percent / tetrahydrofuran / 0.5 h / Ambient temperature 3: 94 percent / 2,6-lutidine, LiI*2H2O / 1 h / 150 °C 4: 72 percent / m-chloroberbenzoic acid / CH2Cl2 / 1 h / Ambient temperature 5: 1.) aq. Na2S2O4, 2.) t-BuOK, O2 / 1.) benzene, 2 min, 2.) t-BuOH, 5 min. View Scheme

1: 10 percent / lithium hexamethyldisilazide / tetrahydrofuran / -78 °C 2: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -10 - 10 °C 3: 1.) NBS, 2.) H2O / 1.) CCl4, 2.) THF,30 h, r.t. 4: 2.) Na, THF-EtOH / 1.) Jones oxidation, 2.) 0 deg C, 5: 68 percent / t-Butylhydroperoxid, RhCl(PPh)3 / benzene / 20 h / 70 °C View Scheme