triethylamine in dichloromethane

1: 75 percent / pyridinium chlorochromate, sodum acetate / CH2Cl2 / 1 h / Ambient temperature 2: 71 percent / tetrahydrofuran / 1 h / 0 °C 3: 91 percent / potassium hydroxide / aq. ethanol / 2.5 h / Ambient temperature 4: 60 percent / pyridine / Ambient temperature 5: thionyl chloride / diethyl ether / 4 h / Ambient temperature 6: 84 percent / pyridine / CH2Cl2 / 2 h / Heating 7: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium(0) / 1.) THF, room temperature, 30 min, 2.) reflux, 2.5 h 8: 76 percent / tetramethylammonium acetate / hexamethylphosphoric acid triamide / 6 h / 90 - 95 °C 9: disodium hydrogen phosphate, 6percent sodium amalgam / tetrahydrofuran; ethanol / 2.5 h / -20 °C 10: 98 percent / hydrogen / 5percent palladium on barium carbonate / ethanol / 2 h / 1520 Torr / Ambient temperature View Scheme

1.1: 1H-imidazole / N,N-dimethyl-formamide / Cooling with ice 2.1: n-butyllithium / tetrahydrofuran; hexanes / -75 °C / Inert atmosphere 2.2: 1 h / -75 °C 3.1: lithium chloride / tetrahydrofuran / 20 °C 3.2: 1 h / -10 °C / Inert atmosphere 4.1: hydrogen / Lindlar's catalyst / ethyl acetate 5.1: sodium tetrahydroborate; methanol / 0.5 h / -7 °C 6.1: 1H-imidazole / N,N-dimethyl-formamide / Cooling with ice 7.1: diisobutylaluminium hydride / toluene / 1 h / -70 °C / Inert atmosphere 8.1: n-butyllithium / tetrahydrofuran / Inert atmosphere; Cooling with ice 9.1: pyridinium p-toluenesulfonate / dichloromethane / 20 °C 10.1: 9-bora-bicyclo[3.3.1]nonane; dihydrogen peroxide / tetrahydrofuran / 3 h / Inert atmosphere; Cooling with ice 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran 12.1: Jone's reagent / water; acetone / 1 h / 0 °C 13.1: trifluoroacetic acid / dichloromethane / 20 °C 14.1: trifluoroacetic acid / dichloromethane / 20 °C View Scheme

1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione

sodium thiosulfate in dichloromethane; sodium hydrogencarbonate; tert-butyl alcohol

1.1: 1H-imidazole / N,N-dimethyl-formamide / Cooling with ice 2.1: n-butyllithium / tetrahydrofuran; hexanes / -75 °C / Inert atmosphere 2.2: 1 h / -75 °C 3.1: lithium chloride / tetrahydrofuran / 20 °C 3.2: 1 h / -10 °C / Inert atmosphere 4.1: hydrogen / Lindlar's catalyst / ethyl acetate 5.1: sodium tetrahydroborate; methanol / 0.5 h / -7 °C 6.1: 1H-imidazole / N,N-dimethyl-formamide / Cooling with ice 7.1: diisobutylaluminium hydride / toluene / 1 h / -70 °C / Inert atmosphere 8.1: n-butyllithium / tetrahydrofuran / Inert atmosphere; Cooling with ice 9.1: pyridinium p-toluenesulfonate / dichloromethane / 20 °C 10.1: 9-bora-bicyclo[3.3.1]nonane; dihydrogen peroxide / tetrahydrofuran / 3 h / Inert atmosphere; Cooling with ice 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran 12.1: Jone's reagent / water; acetone / 1 h / 0 °C 13.1: trifluoroacetic acid / dichloromethane / 20 °C View Scheme

1: 42.06 g / TfOH / CH2Cl2 / 18 h / 0 °C 2: LiAlH4 / tetrahydrofuran / 6 h / Ambient temperature View Scheme

1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2: methanol; N-benzyl-trimethylammonium hydroxide / 1 h / 20 °C View Scheme

1: 98 percent / IBX 2: 43 percent / PPh3; t-BuOK / toluene / -20 °C View Scheme

(i) EtMgBr, Et2O, THF, (ii) /BRN= 1756237/; Multistep reaction;