1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C 1.2: 4 h / 0 - 15 °C 2.1: palladium diacetate; triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 110 °C 3.1: caustic lye / 12 h / 120 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C 1.2: 4 h / 0 - 15 °C 2.1: palladium diacetate; triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 110 °C 3.1: caustic lye / 12 h / 120 °C 4.1: sodium hydroxide / methanol / 1 h / 25 °C View Scheme

1: Methyltriphenylphosphonium bromide With n-butyllithium in tetrahydrofuran; hexane T=0 - 5°C; Wittig Olefination; 1 h; 2: 7-chloro-quinoline-2-carbaldehyde in tetrahydrofuran; hexane; dichloromethane T=0 - 15°C; Wittig Olefination; 4 h;

selenium(IV) oxide in 1,4-dioxane Oxidation; 2.5 h; Heating;