1: With lithium hydroxide hydrate in tetrahydrofuran T=20°C; 20 h; 2: With potassium hydrogensulfate in tetrahydrofuran pH=8;

1.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 1.2: 0.75 h / -78 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 3.2: 2 h / 20 °C 4.1: copper(l) iodide / N,N-dimethyl-formamide / 2.5 h / 100 °C 5.1: lithium hydroxide hydrate / water; tetrahydrofuran / 64 h / 20 °C View Scheme

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 2.2: 2 h / 20 °C 3.1: copper(l) iodide / N,N-dimethyl-formamide / 2.5 h / 100 °C 4.1: lithium hydroxide hydrate / water; tetrahydrofuran / 64 h / 20 °C View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 1.2: 2 h / 20 °C 2.1: copper(l) iodide / N,N-dimethyl-formamide / 2.5 h / 100 °C 3.1: lithium hydroxide hydrate / water; tetrahydrofuran / 64 h / 20 °C View Scheme

1: copper(l) iodide / N,N-dimethyl-formamide / 2.5 h / 100 °C 2: lithium hydroxide hydrate / water; tetrahydrofuran / 64 h / 20 °C View Scheme

nitric acid T=0°C; 0.166667 h;