1: 1) NaH, n-BuLi / 1) THF, 0 deg C, 10 min, 2) THF, 0 deg C, 1 h 2: 99 percent / CF3COOH / CHCl3 / 0.67 h / 23 °C 3: 98 percent / LiBr, DMSO / 0.67 h / 180 °C View Scheme

1: 98 percent / (n-Bu)4NF / tetrahydrofuran / 0.33 h / 23 °C 2: 87 percent / NaH / tetrahydrofuran / 2.5 h 3: 1) NaH, n-BuLi / 1) THF, 0 deg C, 10 min, 2) THF, 0 deg C, 1 h 4: 99 percent / CF3COOH / CHCl3 / 0.67 h / 23 °C 5: 98 percent / LiBr, DMSO / 0.67 h / 180 °C View Scheme

1: imidazole / CH2Cl2 2: 1) n-BuLi / 1) THF, -76 deg C, 10 min, 2) THF, 1 h 3: 90 percent / diisopropylethyl amine / CH2Cl2 / 3.5 h / 23 °C 4: 92 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 5: 97 percent / pyridine / a) 0 deg C, 15 min, b) 20 min 6: 98 percent / (n-Bu)4NF / tetrahydrofuran / 0.33 h / 23 °C 7: 87 percent / NaH / tetrahydrofuran / 2.5 h 8: 1) NaH, n-BuLi / 1) THF, 0 deg C, 10 min, 2) THF, 0 deg C, 1 h 9: 99 percent / CF3COOH / CHCl3 / 0.67 h / 23 °C 10: 98 percent / LiBr, DMSO / 0.67 h / 180 °C View Scheme

cyclooctadiene in 1,4-dioxane T=100°C; Inert atmosphere;

Yield given. Multistep reaction;

1: sodium hydride / dimethylformamide / 1) 20 deg C, 1 h, 2) 90 deg C to 100 deg C, 8 h 2: hydrogen / palladium dichloride, activated carbon / methanol 3: potassium hydroxide / ethanol; H2O / 3 h / Heating View Scheme

trifluorormethanesulfonic acid; oxygen; palladium diacetate in dimethylsulfoxide-d6 T=50°C; 48 h;