1: 77 percent / EtONa / ethanol / 15 h / Ambient temperature 2: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h 3: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 4: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 5: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme

1: 1.) NaH / 1) THF, rt, 1 h; 2) THF, 0 deg C, 5 min, rt, 20 h 2: 15 percent / Pd(PPh3)4, aq. KOH / tetrahydrofuran / 1) rt, overnight; 2) reflux, 24 h View Scheme