1H-imidazole; iodine; triphenylphosphine in tetrahydrofuran T=0°C; Inert atmosphereDarkness;

oxalyl dichloride; dimethyl sulfoxide; triethylamine in dichloromethane T=20°C; Cooling with acetone-dry iceInert atmosphere;

in dichloromethane

triethylamine in dichloromethane

1: Jones reagent 2: sulfonic acid resin View Scheme

chromium(VI) oxide; sulfuric acid; potassium carbonate 1.) H2O, acetone, 2.) acetone, reflux; Yield given. Multistep reaction;

1: 96.6 percent / NEt3, DMAP / CH2Cl2 / 1) 0 deg C, 0.5h, 2) 25 deg C, 4h 2: 1) Cp2Zr(H)Cl, 2) NIS / 1) toluene, 30h, 25 deg C, 2) 62h 4: 80 percent / 5percent HCl / tetrahydrofuran / 216 h / 25 °C View Scheme

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 2.2: 3.5 h / -78 - 20 °C / Inert atmosphere 3.1: zirconocene dichloride; diisobutylaluminium hydride / tetrahydrofuran; n-heptane / 1 h / 0 - 65 °C / Inert atmosphere; Darkness 3.2: 0.25 h / -78 °C / Inert atmosphere 4.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere 4.2: 0.67 h / 0 °C / Inert atmosphere 4.3: 3.5 h / 0 - 20 °C / Inert atmosphere 5.1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C / Inert atmosphere 6.1: n-butyllithium; chloro-trimethyl-silane; triethylamine; diisopropylamine / tetrahydrofuran; hexanes / -78 - 20 °C / Inert atmosphere 6.2: 120 °C / Inert atmosphere 7.1: methanol; diethyl ether; benzene / 1.5 h / 6 - 20 °C / Inert atmosphere 8.1: pyridine; hydrogen fluoride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere 9.1: pyridinium chlorochromate / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere; Celite 10.1: toluene / 110 °C / Inert atmosphere; Molecular sieve; Sealed tube 10.2: 5.58 h / 0 - 20 °C / Molecular sieve 11.1: PHT / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere 11.2: 12 h / 20 °C / Inert atmosphere 12.1: sodium tetrahydroborate / isopropyl alcohol / 77 h / 20 - 50 °C / Inert atmosphere View Scheme

1.1: Jone's reagent / acetone / 0 - 20 °C 2.1: toluene-4-sulfonic acid / dichloromethane / 36 h / Reflux 3.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 °C / Inert atmosphere 4.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 5.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 °C / Inert atmosphere 6.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 7.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 8.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 9.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 9.2: pH 2 / Inert atmosphere View Scheme

1: 99 percent / pyridine / 16 h / 0 °C 2: 92 percent / dimethylsulfoxide / 2 h / 90 °C 3: 97 percent / aq. NaOH / ethanol / 12 h / Heating View Scheme