hydrogen; triethylamine; palladium on activated charcoal in methanol T=25°C; P=760 Torr; 2 h;

1.1: butyllithium / toluene; hexane / 0.75 h / -75 °C 1.2: toluene; hexane / -75 °C 1.3: 73 percent / aq.HCl / H2O / pH 1 2.1: 83 percent / hydrogen; triethylamine / palladium on charcoal / methanol / 2 h / 25 °C / 760 Torr View Scheme

1.1: 73 percent / phosphoric trichloride / 2 h / Heating 2.1: butyllithium / tetrahydrofuran; hexane / 0.75 h / -75 °C 2.2: tetrahydrofuran; hexane / -78 °C 2.3: 31 percent / aq.HCl / H2O / pH 2 3.1: 83 percent / hydrogen; triethylamine / palladium on charcoal / methanol / 2 h / 25 °C / 760 Torr View Scheme

1.1: butyllithium / tetrahydrofuran; hexane / 0.75 h / -75 °C 1.2: tetrahydrofuran; hexane / -78 °C 1.3: 31 percent / aq.HCl / H2O / pH 2 2.1: 83 percent / hydrogen; triethylamine / palladium on charcoal / methanol / 2 h / 25 °C / 760 Torr View Scheme

1.1: isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / 2 h / -10 °C 1.2: tetrahydrofuran; diethyl ether / -78 °C 1.3: 54 percent / aq.HCl / H2O / pH 1 2.1: 72 percent / hydrogen; triethylamine / palladium on charcoal / methanol / 2 h / 25 °C / 760 Torr View Scheme

1.1: 84 percent / phosphoric trichloride / 2 h / Heating 2.1: butyllithium / toluene; hexane / 0.75 h / -75 °C 2.2: toluene; hexane / -75 °C 2.3: 73 percent / aq.HCl / H2O / pH 1 3.1: 83 percent / hydrogen; triethylamine / palladium on charcoal / methanol / 2 h / 25 °C / 760 Torr View Scheme