sodium hydroxide in ethanol Heating;

1.1: sodium hydroxide / ethanol / Reflux 2.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere 5.1: sodium hydroxide / N,N-dimethyl-formamide / 5 h / 140 °C / Inert atmosphere View Scheme

1: With lithium diisopropyl amide in tetrahydrofuran; hexane T=-78°C; 0.5 h; 2: With iodine in tetrahydrofuran; hexane T=-78 - 20°C;

1.1: NaH / tetrahydrofuran / 2 h / 20 °C 1.2: 91 percent / tetrahydrofuran / 8 h / 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 84 percent / iodine / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1.1: NaH / tetrahydrofuran / 2 h / 20 °C 1.2: 91 percent / tetrahydrofuran / 8 h / 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 84 percent / iodine / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1: 89 percent / NaOH / ethanol / Heating 2: 72 percent / piperidine; CuI / Pd(OAc)2(PPh3)2 / dimethylformamide / 5 h / 60 °C View Scheme

1: NaOH / ethanol / Heating 2: 2.50 g / K2CO3 / acetonitrile / Heating View Scheme