1: 99 percent / pyridine; H2 / Lindlar catalyst / pentane / 15 h / 20 °C 2: formic acid / CH2Cl2 / 0.17 h / 20 °C View Scheme

1: 83 percent / toluene / 4 h / Heating 2: 90 percent / n-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 2 min, 2.) -78 deg C, 2-5 min 3: 92 percent / aq. HCl / acetone / 0.33 h / 5 - 20 °C View Scheme

sodium tetrahydroborate; nickel dichloride in methanol; ethanol T=0°C; 3 h;