triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran 2 h; Ambient temperature;

3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane 48 h; Heating;

1: 1) NaH / 1) THF, RT, 10 min, 2) THF, 70 deg C, 10 h 2: 99.4 percent / KOH / ethanol / 30 h / Ambient temperature 3: 1) NaH / 1) THF, Rt, 30 min, 2) THF, 24 h, 70 deg C 4: 72.3 percent / Na2EDTA, NaHCO3, Oxone, MeCOCF3 / acetonitrile / 0.5 h / 0 °C 5: 76.6 percent / pyridinium p-toluenesulfonate / ethanol / 3 h / 55 °C 6: 80.4 percent / PPh3, DEAD / tetrahydrofuran / 2 h / Ambient temperature View Scheme

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

1: 72.3 percent / Na2EDTA, NaHCO3, Oxone, MeCOCF3 / acetonitrile / 0.5 h / 0 °C 2: 76.6 percent / pyridinium p-toluenesulfonate / ethanol / 3 h / 55 °C 3: 80.4 percent / PPh3, DEAD / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: 76.6 percent / pyridinium p-toluenesulfonate / ethanol / 3 h / 55 °C 2: 80.4 percent / PPh3, DEAD / tetrahydrofuran / 2 h / Ambient temperature View Scheme

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