sodium hydride in tetrahydrofuran T=0 - 20°C; 2 h; Inert atmosphereSchlenk technique;

1: NH4OAc / acetic acid / 3 h / Heating 2: Fe, FeCl3, aq. HCl / 1 h / Heating 3: (i) NaOiPr, iPrOH, (ii) /BRN= 969135/ View Scheme

1: Fe, FeCl3, aq. HCl / 1 h / Heating 2: (i) NaOiPr, iPrOH, (ii) /BRN= 969135/ View Scheme

1: 202 mg / t-BuOK / tetrahydrofuran / 1.) 30 min, 2.) 3 d 2: 86 percent / p-TsOH / 2 h / Heating 3: 1.) cerium chloride, 2.) 2percent HCl / 1.) THF, room temperature, 4 h, 2.) 20 min 4: 52 percent / BF3*Et2O / CH2Cl2 / 24 h / Heating View Scheme