lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether T=0°C; 0.333333 h;

1: 1.) aq. sodium hydroxide 2.) oxalyl chloride, pyridine / 1.) 95percent ethanol 2.) benzene, room temp., 3 h 2: 1.) diisopropylamide, n-butyllithium / 1.) THF, -78 deg C, 1 h 2.) THF, -78 deg C, 4 h 3: NaOH / H2O; methanol / 3 h / Heating 4: 20percent HCl / 40 °C 5: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 0.5 h 6: 1.) cupric acetate, pyridine, lead tetraacetate 2.) p-toluenesulfonic acid / 1.) benzene, room temp., 2 h, then 80 deg C, 1 h 2.) benzene, reflux, 3 h View Scheme