ethanol; sodium; ethylamine T=18°C; 24 h;

1: diethyl ether / 1 h / 0 °C 2: 1.) methanesulfonyl chloride / 1.) pyridine, 1 h, 2.) dimethyl sulfoxide, 50-60 deg C, 1 h View Scheme

1: pyridine / 2 h / 0 °C 2: 40 mg / dimethylsulfoxide / 7 h / 60 °C 3: 96 percent / 1.5 M aq. perchloric acid / tetrahydrofuran / 1 h / 0 °C 4: diethyl ether / 1 h / 0 °C 5: 1.) methanesulfonyl chloride / 1.) pyridine, 1 h, 2.) dimethyl sulfoxide, 50-60 deg C, 1 h View Scheme

1: 96 percent / 1.5 M aq. perchloric acid / tetrahydrofuran / 1 h / 0 °C 2: diethyl ether / 1 h / 0 °C 3: 1.) methanesulfonyl chloride / 1.) pyridine, 1 h, 2.) dimethyl sulfoxide, 50-60 deg C, 1 h View Scheme

1: 90 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 5 h / 20 °C 2: 96 percent / pyridinium chlorochromate; silica gel / CH2Cl2 / 2 h / 20 °C 3: 98 percent / DBU / CH2Cl2 / 6 h / 20 °C 4: 95 percent / Zn; KOH / ethanol; H2O / 10 h / Heating 5: 88 percent / CeCl3 / tetrahydrofuran / 3 h / 0 - 20 °C 6: POCl3; pyridine / CH2Cl2 / 3 h / 0 - 20 °C View Scheme

1: 89 percent / pyridinium chlorochromate; silica gel / CH2Cl2 / 0.5 h / 20 °C 2: 86 percent / Li / 1 h / 0 - 20 °C / sonic irradiation 3: 90 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 5 h / 20 °C 4: 96 percent / pyridinium chlorochromate; silica gel / CH2Cl2 / 2 h / 20 °C 5: 98 percent / DBU / CH2Cl2 / 6 h / 20 °C 6: 95 percent / Zn; KOH / ethanol; H2O / 10 h / Heating 7: 88 percent / CeCl3 / tetrahydrofuran / 3 h / 0 - 20 °C 8: POCl3; pyridine / CH2Cl2 / 3 h / 0 - 20 °C View Scheme

1: 90 percent / LAH / diethyl ether / 2 h / 0 - 20 °C 2: 89 percent / pyridinium chlorochromate; silica gel / CH2Cl2 / 0.5 h / 20 °C 3: 86 percent / Li / 1 h / 0 - 20 °C / sonic irradiation 4: 90 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 5 h / 20 °C 5: 96 percent / pyridinium chlorochromate; silica gel / CH2Cl2 / 2 h / 20 °C 6: 98 percent / DBU / CH2Cl2 / 6 h / 20 °C 7: 95 percent / Zn; KOH / ethanol; H2O / 10 h / Heating 8: 88 percent / CeCl3 / tetrahydrofuran / 3 h / 0 - 20 °C 9: POCl3; pyridine / CH2Cl2 / 3 h / 0 - 20 °C View Scheme

1: 88 percent / CeCl3 / tetrahydrofuran / 3 h / 0 - 20 °C 2: POCl3; pyridine / CH2Cl2 / 3 h / 0 - 20 °C View Scheme

1: 1N NaOH / 1 h / 0 °C 2: thionyl chloride / benzene 3: diethyl ether / 3 h / 0 °C 4: aq. NaHCO3 / methanol 5: 22 percent / copper(II) chloride / CHCl3 / 25 h / Heating 6: 83 percent / NaBH4 / methanol / 0.5 h / 0 °C 7: 90 percent / hydrogen / 10percent palladium-carbon / ethyl acetate 8: 99 percent / diethyl ether / 2 h / 0 °C 9: 59 percent / p-TsOH / benzene / 96 h / Ambient temperature View Scheme

1: 90 percent / hydrogen / 10percent palladium-carbon / ethyl acetate 2: 99 percent / diethyl ether / 2 h / 0 °C 3: 59 percent / p-TsOH / benzene / 96 h / Ambient temperature View Scheme