(i) Zn, THF, (ii) /BRN= 1744116/; Multistep reaction;

1: 70 percent / benzene; dimethylformamide / 16 h / Heating 2: 80 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 140 - 145 °C 3: 90 percent / LiAlH4 / diethyl ether / reflux, then room temp., overnight, then reflux, 30 min View Scheme

copper(l) iodide; zinc in ethanol; water 0.75 h; Irradiation;

1: 70 percent / benzene; dimethylformamide / 16 h / Heating 2: 80 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 140 - 145 °C 3: 90 percent / LiAlH4 / diethyl ether / reflux, then room temp., overnight, then reflux, 30 min 4: 90 percent / PBr3, pyridine / diethyl ether / reflux, 20 min, then room temp., overnight, then reflux, 2 h 5: 1)Mg / 1)THF 2)room temp., overnight, then reflux, 3 h 6: 60 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme

diethyl ether; magnesium anschliessendes Erwaermen;

1.1: EtMgBr / tetrahydrofuran / 2 h / 20 °C 1.2: cuprous cyanide / hexamethylphosphoric acid triamide; tetrahydrofuran / 50 °C 2.1: conc. H2SO4 / CCl4 / Heating View Scheme

1: 1.) t-BuLi / 1.) THF, 2.) THF, -50 deg C, 1 h 2: bipyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 3: I2 / diethyl ether / 4 h / Ambient temperature 4: NaBH4 / methanol / 0.25 h / 0 °C 5: imidazole / dimethylformamide / 2.5 h / 50 °C 6: diisobutylaluminium hydride / CH2Cl2 / 0.08 h / -78 °C 7: pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 8: 83 percent / 48percent aq. HF / acetonitrile / 2 h / Ambient temperature View Scheme

1: 1.) C2H5MgBr, 2.) cuprous chloride / 1.) THF, reflux, 3 h, 2.) a). 20 deg C, 2 h, b). 65 deg C, 12 h 2: 90 percent / hydrogen, nickel acetate, sodium borohydride, ethylenediamine / ethanol View Scheme

1: 1.) t-BuLi / 1.) THF, 2.) THF, -50 deg C, 1 h 2: bipyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 3: I2 / diethyl ether / 4 h / Ambient temperature 4: NaBH4 / methanol / 0.25 h / 0 °C 5: imidazole / dimethylformamide / 2.5 h / 50 °C 6: diisobutylaluminium hydride / CH2Cl2 / 0.08 h / -78 °C 7: pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 8: 83 percent / 48percent aq. HF / acetonitrile / 2 h / Ambient temperature 9: 85 percent / pyridine / 4 h / Ambient temperature 10: t-BuOK / tetrahydrofuran 11: 100 percent / LiOH / propan-2-ol; H2O View Scheme

1: 1.) ethylmagnesium bromide, copper(I) bromide / 1.) THF, -78 -> 25 deg C, 2.) -78 -> 25 deg C 2: H2 / Lindlar catalyst / hexane / 25 °C 3: KF / dimethylformamide / 25 °C 4: 90 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 12 h / 25 °C 5: 60 percent / H2 / Lindlar catalyst / hexane / 25 °C 6: 75 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 7: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme