acetic acid; Adam's catalyst in hydrogen; ethyl acetate

thionyl chloride; sulfuric acid; palladium monocarbide in 1,4-dioxane; methanol; ethanol; 2-Nitropropane; benzene

sodium hydroxide; sodium acetate in water; acetic acid

hydrogen in ethanol P=1810.02 Torr; 24 h;

1: 1.) LDA, hexamethylphosphoramide / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, RT, overnight 2: triethylamine / H2O; acetone / 0 °C 3: NaN3 / H2O; acetone / 0.75 h / Ambient temperature 4: toluene / 0.5 h / Heating 5: Heating 6: H2 / ethanol / 24 h / 1810.02 Torr View Scheme

1: triethylamine / H2O; acetone / 0 °C 2: NaN3 / H2O; acetone / 0.75 h / Ambient temperature 3: toluene / 0.5 h / Heating 4: Heating 5: H2 / ethanol / 24 h / 1810.02 Torr View Scheme