lithium aluminium tetrahydride in diethyl ether 4 h; Ambient temperature;

1: 68 percent / sodamide 2: 72 percent / dimethylformamide / 24 h / Heating 3: 75 percent / p-TsOH / toluene / 6 h / Heating 4: 90 percent / H2 / 10percent palladium-charcoal / aq. ethanol 5: 95 percent / NaOCl / H2O; CH2Cl2 / 3 h / dark 6: 1.) CF3COOH, 2.) potassium carbonate / 1.) MeOH, reflux, 3 h, 2.) reflux, 1 h View Scheme

1: 72 percent / dimethylformamide / 24 h / Heating 2: 75 percent / p-TsOH / toluene / 6 h / Heating 3: 90 percent / H2 / 10percent palladium-charcoal / aq. ethanol 4: 95 percent / NaOCl / H2O; CH2Cl2 / 3 h / dark 5: 1.) CF3COOH, 2.) potassium carbonate / 1.) MeOH, reflux, 3 h, 2.) reflux, 1 h View Scheme

1: 90 percent / H2 / 10percent palladium-charcoal / aq. ethanol 2: 95 percent / NaOCl / H2O; CH2Cl2 / 3 h / dark 3: 1.) CF3COOH, 2.) potassium carbonate / 1.) MeOH, reflux, 3 h, 2.) reflux, 1 h View Scheme

1: 75 percent / p-TsOH / toluene / 6 h / Heating 2: 90 percent / H2 / 10percent palladium-charcoal / aq. ethanol 3: 95 percent / NaOCl / H2O; CH2Cl2 / 3 h / dark 4: 1.) CF3COOH, 2.) potassium carbonate / 1.) MeOH, reflux, 3 h, 2.) reflux, 1 h View Scheme

1: 95 percent / NaOCl / H2O; CH2Cl2 / 3 h / dark 2: 1.) CF3COOH, 2.) potassium carbonate / 1.) MeOH, reflux, 3 h, 2.) reflux, 1 h View Scheme

1: 77.5 percent / toluene-4-sulphonic acid / toluene / 4 h / Heating 2: 88 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature View Scheme

1: 67.5 percent / ethanol / 120 h / Ambient temperature 2: 77.5 percent / toluene-4-sulphonic acid / toluene / 4 h / Heating 3: 88 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature View Scheme

potassium carbonate; trifluoroacetic acid 1.) MeOH, reflux, 3 h, 2.) reflux, 1 h; Yield given. Multistep reaction;