disodium hydrogenphosphate; sodium amalgam in methanol T=0°C; 2 h;

disodium hydrogenphosphate; sodium amalgam in methanol T=0°C; 2 h;

1: 89 percent / H2 / 10percent Pd/C / methanol / 3102.9 Torr / Ambient temperature 2: 96 percent / 6percent Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C View Scheme

1: 85 percent / pyridine / 24 h / 0 °C 2: 99 percent / K2CO3 / H2O; dimethylformamide / 24 h / Ambient temperature 3: 1.) Ti(Oi-Pr)4, 2.) KHMDS / 1.) THF, -78 deg C, 10 min, 2.) -70 deg C, 2 h 4: 89 percent / H2 / 10percent Pd/C / methanol / 3102.9 Torr / Ambient temperature 5: 96 percent / 6percent Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C View Scheme

1: 94 percent / 4M HCl / tetrahydrofuran / 3 h / Ambient temperature 2: 85 percent / pyridine / 24 h / 0 °C 3: 99 percent / K2CO3 / H2O; dimethylformamide / 24 h / Ambient temperature 4: 1.) Ti(Oi-Pr)4, 2.) KHMDS / 1.) THF, -78 deg C, 10 min, 2.) -70 deg C, 2 h 5: 89 percent / H2 / 10percent Pd/C / methanol / 3102.9 Torr / Ambient temperature 6: 96 percent / 6percent Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C View Scheme

1: 99 percent / K2CO3 / H2O; dimethylformamide / 24 h / Ambient temperature 2: 1.) Ti(Oi-Pr)4, 2.) KHMDS / 1.) THF, -78 deg C, 10 min, 2.) -70 deg C, 2 h 3: 89 percent / H2 / 10percent Pd/C / methanol / 3102.9 Torr / Ambient temperature 4: 96 percent / 6percent Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C View Scheme

1: 63 percent / K2CO3 / dimethylformamide / 48 h / 80 °C 2: 94 percent / aq. HCl / tetrahydrofuran / 3 h / Ambient temperature 3: 85 percent / pyridine / 24 h / 0 °C 4: 99 percent / K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature 5: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C 6: 89 percent / H2 / Pd/C / methanol / 3102.9 Torr / Ambient temperature 7: 96 percent / Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C View Scheme

1: 89 percent / H2 / 10percent Pd/C / methanol / 3102.9 Torr / Ambient temperature 2: 96 percent / 6percent Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C View Scheme

1: 89 percent / H2 / Pd/C / methanol / 3102.9 Torr / Ambient temperature 2: 96 percent / Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C View Scheme

1: 1.) Ti(Oi-Pr)4, 2.) KHMDS / 1.) THF, -78 deg C, 10 min, 2.) -70 deg C, 2 h 2: 89 percent / H2 / 10percent Pd/C / methanol / 3102.9 Torr / Ambient temperature 3: 96 percent / 6percent Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C View Scheme