sodium hydroxide in methanol 20 h; Heating;

1: 100 percent / 15 h / 140 °C 2: 1.) NaN(SiCH3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, b) r.t., 15 h 3: 97 percent / H2 / 10percent Pd/C / ethyl acetate 4: 95 percent / NaOH / methanol / 20 h / Heating View Scheme

1: 87 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 1.) NaN(SiCH3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, b) r.t., 15 h 3: 97 percent / H2 / 10percent Pd/C / ethyl acetate 4: 95 percent / NaOH / methanol / 20 h / Heating View Scheme

1: 1.) NaN(SiCH3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, b) r.t., 15 h 2: 97 percent / H2 / 10percent Pd/C / ethyl acetate 3: 95 percent / NaOH / methanol / 20 h / Heating View Scheme

1: 1.) NaN(SiCH3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, b) r.t., 15 h 2: 97 percent / H2 / 10percent Pd/C / ethyl acetate 3: 95 percent / NaOH / methanol / 20 h / Heating View Scheme

1: 73 percent / 48percent hydrobromic acid / benzene / 36 h / Heating 2: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 3: 1) magnesium, 2) Li2CuCl4 / 1) THF, 2) room temperature, 3 h 4: NaOH / ethanol / 2 h / Heating 5: 2 N HCl / ethanol / 1 h / Heating View Scheme

1: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 2: 1) magnesium, 2) Li2CuCl4 / 1) THF, 2) room temperature, 3 h 3: NaOH / ethanol / 2 h / Heating 4: 2 N HCl / ethanol / 1 h / Heating View Scheme

1: 98 percent / 98percent sulfuric acid / 5 h / Heating 2: 99 percent / LiAlH4 / diethyl ether / 0.5 h 3: 73 percent / 48percent hydrobromic acid / benzene / 36 h / Heating 4: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 5: 1) magnesium, 2) Li2CuCl4 / 1) THF, 2) room temperature, 3 h 6: NaOH / ethanol / 2 h / Heating 7: 2 N HCl / ethanol / 1 h / Heating View Scheme

1: 99 percent / LiAlH4 / diethyl ether / 0.5 h 2: 73 percent / 48percent hydrobromic acid / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 1) magnesium, 2) Li2CuCl4 / 1) THF, 2) room temperature, 3 h 5: NaOH / ethanol / 2 h / Heating 6: 2 N HCl / ethanol / 1 h / Heating View Scheme

1: 1) magnesium, 2) Li2CuCl4 / 1) THF, 2) room temperature, 3 h 2: NaOH / ethanol / 2 h / Heating 3: 2 N HCl / ethanol / 1 h / Heating View Scheme