1: NaBH4 / diethyl ether; methanol / 0.75 h 2: 92 percent / 1.) 98percent HCOOH; 2.) aq. KOH / 3 h / 20 °C 3: 231 mg / pyridine / 30 °C 4: 78 percent / LiAlH4 / diethyl ether / 0.5 h / Heating View Scheme

暂无反应条件数据

1: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h 2: 94 percent / SOCl2, pyridine / benzene / 16 h / Ambient temperature 3: 91 percent / MeOK / toluene / 2 h / Ambient temperature 4: 1.) MeOK / 1.) cyclohexane, 38 deg C, 2 h View Scheme

1: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h 2: 94 percent / SOCl2, pyridine / benzene / 16 h / Ambient temperature 3: 91 percent / MeOK / toluene / 2 h / Ambient temperature 4: 1.) MeOK / 1.) cyclohexane, 38 deg C, 2 h View Scheme

1: 72 percent / NaBH4 / methanol / 5 h / -10 °C 2: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 4: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 5: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 6: 78 percent / dimethylformamide / 24 h / Ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 9: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 10: 1.) n-BuLi, 3.) H2O, KOH 11: 70 percent / Li, ethylamine / diethyl ether 12: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 13: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 23 °C / |Inert atmosphere 1.2: 24 h / 0 °C / |Inert atmosphere 2.1: magnesium; dilithium tetrachlorocuprate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 3.1: o,o'-dichloro-BINOL; antimony(V) pentachloride / dichloromethane / 0.25 h / -78 °C / |Inert atmosphere 4.1: water; potassium permanganate; sodium periodate; sodium carbonate / tert-butyl alcohol / 12 h / 23 °C / |Inert atmosphere View Scheme

manganese(IV) oxide in hexane; chloroform 5 h; Ambient temperature;

sulfuric acid; Copper(I)chloride in 1,4-dioxane; water

selenium(IV) oxide in ethanol RefluxInert atmosphere; regioselective reaction;

tert.-butylhydroperoxide; selenium(IV) oxide; salicylic acid in dichloromethane T=20°C; 24 h;