1: methanol; potassium fluoride 2: N-bromosuccinmide; silver nitrate / acetone View Scheme

tetrabutyl ammonium fluoride in tetrahydrofuran T=-20°C; 0.5 h;

sodium hydroxide in ethanol T=20°C; 18 h;

sodium hydroxide; water

1: LiAlH4 / tetrahydrofuran / 2 h / 23 °C 2: 1.01 g / K2CO3; MeOH / 22 h / 23 °C View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 2.1: 1H-imidazole / tetrahydrofuran / 15 h / 0 - 20 °C / |Inert atmosphere 3.1: potassium carbonate; methanol / 2 h / 20 °C / |Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / |Inert atmosphere 4.2: 0.5 h / 20 °C / |Inert atmosphere 5.1: hydrogen; palladium 10 on activated carbon / ethyl acetate / 15001.5 Torr 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 7.1: triethylamine / dichloromethane / 0.5 h / 0 °C / |Inert atmosphere 8.1: sodium iodide / acetone / 0.25 h / 20 °C 9.1: N,N-dimethyl-formamide / 2 h / 20 °C / |Inert atmosphere 10.1: sodium hydroxide; water / 4 h / |Reflux View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 0.5 h; Inert atmosphere;

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine T=90°C; 0.5 h; Inert atmosphere;

triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide in tetrahydrofuran T=20°C; 8 h;

triethylamine; triphenylphosphine; palladium diacetate in hydrogenchloride