1: sodium borohydride, 2N HCl / 3 h / 0 - 5 °C 2: titanium(IV) chloride / CH2Cl2 / 3.5 h / Ambient temperature 3: 16 percent / lithium aluminum hydride / diethyl ether / 1 h / Heating 4: 65 percent / H2, conc. HCl / 10percent palladium on C / ethanol / 15 h / 3040 Torr / Ambient temperature View Scheme

lithium triethylborohydride in tetrahydrofuran T=-78°C;

1: sodium borohydride, 2N HCl / 3 h / 0 - 5 °C 2: titanium(IV) chloride / CH2Cl2 / 3.5 h / Ambient temperature 3: 16 percent / lithium aluminum hydride / diethyl ether / 1 h / Heating 4: 65 percent / H2, conc. HCl / 10percent palladium on C / ethanol / 15 h / 3040 Torr / Ambient temperature View Scheme