AlCl3, aluminium chloride; lithium aluminium tetrahydride in tetrahydrofuran T=-25 - -20°C; 1 h; Solvent;

sodium hydrogencarbonate in toluene T=25°C; 0.5 h;

1.1: potassium carbonate; copper / o-xylene / 25 - 30 °C / Reflux 2.1: thionyl chloride / N,N-dimethyl-formamide; toluene / 40 - 50 °C 2.2: 0 - 30 °C 3.1: potassium tert-butylate / toluene / 15 - 30 °C / Inert atmosphere 3.2: 0 - 5 °C / pH 2 - 2.5 4.1: phosphorus pentoxide; phosphoric acid / 100 - 120 °C 5.1: magnesium / methanol / 25 - 65 °C / Reflux 6.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / -5 - 5 °C 6.2: -5 - 5 °C View Scheme

1.1: caesium carbonate / copper(l) chloride; N,N-dimethylaminoacetic acid / 1,4-dioxane / 110 - 115 °C 1.2: 5 h / 25 - 65 °C 2.1: hydrogenchloride / dichloromethane; water / pH 1.5 2.2: 0.75 h / 0 - 15 °C 3.1: potassium tert-butylate / toluene / 3 h / 20 °C 3.2: 3 h / 20 °C 4.1: phosphorous pentoxide; phosphoric acid / 96 h / 115 - 120 °C 5.1: formic acid; iodine; magnesium / toluene; methanol / 5 h / 20 - 40 °C 5.2: 5 - 10 °C / pH ~ 1 6.1: sodium tetrahydroborate / tetrahydrofuran / 0.25 h / 20 °C 6.2: 6 h / Reflux 6.3: 10 - 15 °C View Scheme

1.1: magnesium / methanol / 25 - 65 °C / Reflux 2.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / -5 - 5 °C 2.2: -5 - 5 °C View Scheme

1.1: potassium carbonate; copper / o-xylene / 25 - 30 °C / Reflux 2.1: thionyl chloride / N,N-dimethyl-formamide; toluene / 40 - 50 °C 2.2: 0 - 30 °C 3.1: potassium tert-butylate / toluene / 15 - 30 °C / Inert atmosphere 3.2: 0 - 5 °C / pH 2 - 2.5 4.1: phosphorus pentoxide; phosphoric acid / 100 - 120 °C 5.1: magnesium / methanol / 25 - 65 °C / Reflux 6.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / -5 - 5 °C 6.2: -5 - 5 °C View Scheme

1.1: thionyl chloride / N,N-dimethyl-formamide; toluene / 40 - 50 °C 1.2: 0 - 30 °C 2.1: potassium tert-butylate / toluene / 15 - 30 °C / Inert atmosphere 2.2: 0 - 5 °C / pH 2 - 2.5 3.1: phosphorus pentoxide; phosphoric acid / 100 - 120 °C 4.1: magnesium / methanol / 25 - 65 °C / Reflux 5.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / -5 - 5 °C 5.2: -5 - 5 °C View Scheme

1.1: potassium tert-butylate / toluene / 15 - 30 °C / Inert atmosphere 1.2: 0 - 5 °C / pH 2 - 2.5 2.1: phosphorus pentoxide; phosphoric acid / 100 - 120 °C 3.1: magnesium / methanol / 25 - 65 °C / Reflux 4.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / -5 - 5 °C 4.2: -5 - 5 °C View Scheme

1: xylene / 20 h / Reflux 2: potassium tert-butylate / tetrahydrofuran / 24 h / 10 - 20 °C / Inert atmosphere; Cooling with ice 3: lithium hexamethyldisilazane / tetrahydrofuran / 18 h / Inert atmosphere; Reflux 4: caesium carbonate; copper(l) iodide; N,N-dimethylaminoacetic acid / N,N-dimethyl-formamide / 3.5 h / 140 °C / Inert atmosphere View Scheme

1: potassium tert-butylate / tetrahydrofuran / 24 h / 10 - 20 °C / Inert atmosphere; Cooling with ice 2: lithium hexamethyldisilazane / tetrahydrofuran / 18 h / Inert atmosphere; Reflux 3: caesium carbonate; copper(l) iodide; N,N-dimethylaminoacetic acid / N,N-dimethyl-formamide / 3.5 h / 140 °C / Inert atmosphere View Scheme