1.1: potassium carbonate / acetone / 5 h / Reflux 2.1: N,N-dimethyl-aniline / Inert atmosphere; Reflux 2.2: 25 °C 3.1: ozone / dichloromethane / -78 - 20 °C / Inert atmosphere 3.2: 20 °C 4.1: toluene-4-sulfonic acid / toluene / 0.75 h / Reflux 5.1: hydrogen / triethylamine; 5 Pd(II)/C(eggshell) / ethanol; tetrahydrofuran / 24 h / 35 °C / 4500.45 - 5250.53 Torr 6.1: sodium methylate / tetrahydrofuran / 1 h / 20 °C 6.2: 2.25 h / 20 °C View Scheme

sulfuric acid; potassium nitrate T=-10°C;

1: KNO3, H2SO4 2: H2 / Raney-Ni / ethanol View Scheme

1: 74 percent / sodium methoxide / methanol / 50 h / Heating 2: sodium borohydride / methanol / 0.33 h / Ambient temperature 3: toluene-p-sulphonic acid / benzene / 1.5 h / Heating 4: 80 percent / sodium carbonate, water / dioxane / 5.5 h / Heating View Scheme

1: K2CO3, CuO, Py 2: (i) NaOEt, EtOH, 1,2-dimethoxy-ethane, (ii) aq. H2SO4 View Scheme

pyridine; potassium carbonate; copper(II) oxide

sodium hydroxide