oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane 1 h; Inert atmosphere;

1: 67 percent / HBr / petroleum ether / 0.75 h / 15 °C 2: SOCl2 View Scheme

1: 10 percent / Et3N / diethyl ether / 0.5 h / Ambient temperature 2: 84.4 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 3: 94 percent / NaIO4 / H2O; methanol / 20 h / Ambient temperature 4: LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 30 min, ice bath 5: Al-Hg / tetrahydrofuran; H2O / 6 h / Heating View Scheme

triethylamine in methanol; water

暂无反应条件数据

1: dihydrogen peroxide / pyridine; diethyl ether / 1.75 h / 0 - 20 °C 2: acetic acid / 20 h / 100 °C 3: potassium borohydride / methanol / 0.5 h / 0 °C View Scheme

lithium aluminium tetrahydride

1: AlCl3 / dimethylformamide / 1 h / 90 °C 2: 85 percent / dimethylsulfoxide / 2 h / 80 °C 3: 95 percent / NH2NH2*H2O, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 4: 95 percent / diethyl ether / 12 h / 0 °C 5: 90 percent / LiAlH4 / diethyl ether / 4 h / Heating 6: 88 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 7: 1.) n-BuLi / 1.) THF, -78 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) RT, 45 min 8: 89 percent / concd H2SO4 / 24 h / Heating 9: 95 percent / LiAlH4 / diethyl ether / 4 h / Heating 10: 85 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 11: 82 percent / dimethylsulfoxide / 2 h / 80 °C 12: 91 percent / KOH / ethane-1,2-diol / 6 h / Heating 13: 95 percent / diethyl ether / 12 h / 0 °C 14: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 15: 95 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: NH3 / 0 °C 2: P2O5 / 250 °C View Scheme

1: Et3N / CH2Cl2 / Ambient temperature 2: (i) iBu2AlH, toluene, (ii) aq. H2SO4, Na2SO4 View Scheme