1: 99.4 percent / KOH / ethanol / 30 h / Ambient temperature 2: 1) NaH / 1) THF, Rt, 30 min, 2) THF, 24 h, 70 deg C 3: 72.3 percent / Na2EDTA, NaHCO3, Oxone, MeCOCF3 / acetonitrile / 0.5 h / 0 °C 4: 76.6 percent / pyridinium p-toluenesulfonate / ethanol / 3 h / 55 °C 5: 80.4 percent / PPh3, DEAD / tetrahydrofuran / 2 h / Ambient temperature View Scheme

lithium aluminium tetrahydride in diethyl ether T=0 - 20°C;

1: 92 percent / KOAc / dimethylsulfoxide / 6 h / 80 °C 2: 85 percent / p-TsOH / ethanol / 12 h / Ambient temperature View Scheme