sodium hydride; tetra-(n-butyl)ammonium iodide in tetrahydrofuran; Petroleum ether 3 h;

sodium hydroxide; barium carbonate in methanol

sulfuric acid; copper(II) sulfate Erwaermen einer Loesung des Reaktionsprodukts in Xylol mit Benzylchlorid und Kaliumhydroxid;

1: 100 percent / pyridine / CH2Cl2 / 0.5 h / -5 °C 2: Na2SO4 / CH2Cl2 / 72 h / Ambient temperature View Scheme

sodium sulfate in dichloromethane 72 h; Ambient temperature; Yield given;

1: 8.53 g / toluene-p-sulfonic acid / 20 h / 20 °C 2: NaH / dimethylformamide View Scheme

1: H2SO4 / 20 h / 20 °C 2: 8.53 g / toluene-p-sulfonic acid / 20 h / 20 °C 3: NaH / dimethylformamide View Scheme

1.1: methanol; potassium carbonate / 3 h / 20 °C 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 3.2: -78 - 20 °C / Inert atmosphere 4.1: diisobutylaluminium hydride / hexane / 1.5 h / 0 °C / Inert atmosphere 5.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 - 20 °C / Inert atmosphere 7.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve 7.2: 0.67 h / 5 °C 8.1: bis(benzonitrile)palladium(II) dichloride; p-benozquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 9.1: ozone / methanol / 0.5 h / -78 °C 9.2: 0 - 20 °C 10.1: sodium hydride / tetrahydrofuran / 5 - 20 °C 10.2: 5 - 20 °C View Scheme

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / hexane / 1.5 h / 0 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 - 20 °C / Inert atmosphere 6.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve 6.2: 0.67 h / 5 °C 7.1: bis(benzonitrile)palladium(II) dichloride; p-benozquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 8.1: ozone / methanol / 0.5 h / -78 °C 8.2: 0 - 20 °C 9.1: sodium hydride / tetrahydrofuran / 5 - 20 °C 9.2: 5 - 20 °C View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / hexane / 1.5 h / 0 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 - 20 °C / Inert atmosphere 5.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve 5.2: 0.67 h / 5 °C 6.1: bis(benzonitrile)palladium(II) dichloride; p-benozquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 7.1: ozone / methanol / 0.5 h / -78 °C 7.2: 0 - 20 °C 8.1: sodium hydride / tetrahydrofuran / 5 - 20 °C 8.2: 5 - 20 °C View Scheme