hydrogen fluoride in water; acetonitrile 0.5 h; Ambient temperature;

1: hydrogen / 5percent palladium on carbon / methanol 2: 78 percent / diethyl phosphorocyanidate, triethylamine / dimethylformamide 3: 89 percent / p-toluenesulfonic acid / benzene / Heating 4: 76 percent / diisobutylaluminum hydride / diethyl ether / 1 h / -20 °C 5: 83 percent / tetrahydrofuran / 1.) -15 deg C, 1 h, 2.) room temperature, 2 h 6: 93 percent / 46percent hydrogen fluoride / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme

1: 86 percent / H2 / Raney nickel / acetone 2: 84 percent / phenol, hexamethyldisilazane / benzene / Heating 3: 1.) lithium di-isopropylamide, 2.) 2M HCl / 1.) -78 deg C, 1 h, THF, 2.) ether View Scheme

1: 82 percent / 10percent aq. sodium hydroxide / 96 h 2: 86 percent / H2 / Raney nickel / acetone 3: 84 percent / phenol, hexamethyldisilazane / benzene / Heating 4: 1.) lithium di-isopropylamide, 2.) 2M HCl / 1.) -78 deg C, 1 h, THF, 2.) ether View Scheme

1: 78 percent / diethyl phosphorocyanidate, triethylamine / dimethylformamide 2: 89 percent / p-toluenesulfonic acid / benzene / Heating 3: 76 percent / diisobutylaluminum hydride / diethyl ether / 1 h / -20 °C 4: 83 percent / tetrahydrofuran / 1.) -15 deg C, 1 h, 2.) room temperature, 2 h 5: 93 percent / 46percent hydrogen fluoride / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme

1: 89 percent / p-toluenesulfonic acid / benzene / Heating 2: 76 percent / diisobutylaluminum hydride / diethyl ether / 1 h / -20 °C 3: 83 percent / tetrahydrofuran / 1.) -15 deg C, 1 h, 2.) room temperature, 2 h 4: 93 percent / 46percent hydrogen fluoride / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme

1: 83 percent / tetrahydrofuran / 1.) -15 deg C, 1 h, 2.) room temperature, 2 h 2: 93 percent / 46percent hydrogen fluoride / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme

1: 97 percent / p-toluenesulfonic acid / benzene / Heating 2: 76 percent / diisobutylaluminum hydride / diethyl ether / 1 h / -20 °C 3: 83 percent / tetrahydrofuran / 1.) -15 deg C, 1 h, 2.) room temperature, 2 h 4: 93 percent / 46percent hydrogen fluoride / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme

1: 76 percent / diisobutylaluminum hydride / diethyl ether / 1 h / -20 °C 2: 83 percent / tetrahydrofuran / 1.) -15 deg C, 1 h, 2.) room temperature, 2 h 3: 93 percent / 46percent hydrogen fluoride / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme

1: 84 percent / phenol, hexamethyldisilazane / benzene / Heating 2: 1.) lithium di-isopropylamide, 2.) 2M HCl / 1.) -78 deg C, 1 h, THF, 2.) ether View Scheme