hydrogenchloride T=0°C; 0.5 h; Yield given;

1: HCl / 0.5 h / 0 °C 2: Ambient temperature 3: Ti(OiPr)4 / tetrahydrofuran; toluene / 60 h / 100 °C 4: H2, aq. HCl / 10 percent Pd/C / 5 h / 50 °C / 3750.3 Torr 5: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature 6: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C View Scheme

1: HCl / 0.5 h / 0 °C 2: Ambient temperature 3: Ti(OiPr)4 / tetrahydrofuran; toluene / 60 h / 100 °C 4: H2, aq. HCl / 10 percent Pd/C / 5 h / 50 °C / 3750.3 Torr View Scheme

1: HCl / 0.5 h / 0 °C 2: Ambient temperature 3: Ti(OiPr)4 / tetrahydrofuran; toluene / 60 h / 100 °C 4: H2, aq. HCl / 10 percent Pd/C / 5 h / 50 °C / 3750.3 Torr 5: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature View Scheme