copper(II) nitrate in acetic anhydride T=-20°C;

1: 94 percent / sodium amide / tetrahydrofuran / 15 h / 45 °C 2: 1.) butyllithium / 1.) Et2O, 2.) -78 deg C, 10 min 3: 83 percent / 60percent HClO4 / tetrahydrofuran / 5 h / 70 °C 4: diethyl ether / 1.5 h / 0 °C 5: 17 percent / N-bromosuccinimide / aq. acetic acid / 1 h / 25 °C 6: 1.) H2, 2.) potassium carbonate / 1.) 5percent Pd-C / 1.) acetone 7: 80 percent / copper(II) nitrate / acetic anhydride / -20 °C View Scheme

1: 1.) butyllithium / 1.) Et2O, 2.) -78 deg C, 10 min 2: 83 percent / 60percent HClO4 / tetrahydrofuran / 5 h / 70 °C 3: diethyl ether / 1.5 h / 0 °C 4: 17 percent / N-bromosuccinimide / aq. acetic acid / 1 h / 25 °C 5: 1.) H2, 2.) potassium carbonate / 1.) 5percent Pd-C / 1.) acetone 6: 80 percent / copper(II) nitrate / acetic anhydride / -20 °C View Scheme

1: diethyl ether / 1.5 h / 0 °C 2: 17 percent / N-bromosuccinimide / aq. acetic acid / 1 h / 25 °C 3: 1.) H2, 2.) potassium carbonate / 1.) 5percent Pd-C / 1.) acetone 4: 80 percent / copper(II) nitrate / acetic anhydride / -20 °C View Scheme

1: 17 percent / N-bromosuccinimide / aq. acetic acid / 1 h / 25 °C 2: 1.) H2, 2.) potassium carbonate / 1.) 5percent Pd-C / 1.) acetone 3: 80 percent / copper(II) nitrate / acetic anhydride / -20 °C View Scheme

1: 80 percent / Jones reagent 2: 86 percent / 60percent HClO4 / tetrahydrofuran / 0.83 h / 50 °C 3: 17 percent / N-bromosuccinimide / aq. acetic acid / 1 h / 25 °C 4: 1.) H2, 2.) potassium carbonate / 1.) 5percent Pd-C / 1.) acetone 5: 80 percent / copper(II) nitrate / acetic anhydride / -20 °C View Scheme

1: 86 percent / 60percent HClO4 / tetrahydrofuran / 0.83 h / 50 °C 2: 17 percent / N-bromosuccinimide / aq. acetic acid / 1 h / 25 °C 3: 1.) H2, 2.) potassium carbonate / 1.) 5percent Pd-C / 1.) acetone 4: 80 percent / copper(II) nitrate / acetic anhydride / -20 °C View Scheme

1: 83 percent / 60percent HClO4 / tetrahydrofuran / 5 h / 70 °C 2: diethyl ether / 1.5 h / 0 °C 3: 17 percent / N-bromosuccinimide / aq. acetic acid / 1 h / 25 °C 4: 1.) H2, 2.) potassium carbonate / 1.) 5percent Pd-C / 1.) acetone 5: 80 percent / copper(II) nitrate / acetic anhydride / -20 °C View Scheme

1: 1.) H2, 2.) potassium carbonate / 1.) 5percent Pd/C / 1.) acetone 2: 100 percent / Zn, 10percent NaOH / dioxane; H2O / 12 h / 70 °C 3: 80 percent / copper(II) nitrate / acetic anhydride / -20 °C View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium formate in N,N-dimethyl-formamide T=100°C; 3 h;