1: 1.) sodium, ethanol / 1.) 15 min., 2.) THF, 60 deg C, 5h 2: 92 percent / NaOH / aq. ethanol / 5 h / Heating 3: 1.) PCl5, 2.) AlCl3 / 1.) CS2, 65 deg C, 6h, 2.) CH2Cl2, 55-60 deg C, 23h 4: 1.) KH / 1.) THF, 5h, r.t. 2.) THF View Scheme

1: 1.) sodium, ethanol / 1.) 15 min., 2.) THF, 60 deg C, 5h 2: 92 percent / NaOH / aq. ethanol / 5 h / Heating 3: 1.) PCl5, 2.) AlCl3 / 1.) CS2, 65 deg C, 6h, 2.) CH2Cl2, 55-60 deg C, 23h 4: 1.) KH / 1.) THF, 5h, r.t., 2.) THF, 24 h View Scheme

1: 1.) sodium, ethanol / 1.) 15 min., 2.) THF, 60 deg C, 5h 2: 92 percent / NaOH / aq. ethanol / 5 h / Heating 3: 1.) PCl5, 2.) AlCl3 / 1.) CS2, 65 deg C, 6h, 2.) CH2Cl2, 55-60 deg C, 23h 4: 73 percent / LiAlH4 / tetrahydrofuran / 5 h / Heating View Scheme

1: 70 percent / NaOEt / diethyl ether / 24 h / Ambient temperature 2: 40 percent / KOH / ethanol; H2O / 6 h / Heating 3: 60 percent / urea / xylene / Heating View Scheme

sodium ethanolate in ethanol 4 h; Heating;

1: 70 percent / NaOEt / diethyl ether / 24 h / Ambient temperature 2: 40 percent / KOH / ethanol; H2O / 6 h / Heating 3: 60 percent / urea / xylene / Heating 4: 65 percent / sodium bis(2-methoxyethoxy)aluminum hydride / benzene / 2 h / Heating View Scheme

1: 82 percent / 15-crown-5; sodium azide / benzene / 8 h / 20 °C 2: 71 percent / p-toluenesulfonic acid monohydrate; hydrogen / Pd/C / aq. ethanol / 24 h / 20 °C / 5171.48 Torr 3: 80 percent / pyridine / CH2Cl2 / 8 h / 20 °C 4: 81 percent / LiOH*H2O / ethanol / 20 h / 20 °C View Scheme