sodium tetrahydroborate in ethanol T=55 - 60°C; 1.83333 h;

isopropyl alcohol

1: 84 percent / HF (g) 2: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C View Scheme

1: conc. H2SO4 / benzene / 3 h / Heating 2: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 3: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 4: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 5: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 6: KOH / ethanol / 1 h / Heating 7: 84 percent / HF (g) 8: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C View Scheme

1: KOH / ethanol / 1 h / Heating 2: 84 percent / HF (g) 3: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C View Scheme

1: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 2: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 3: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 4: KOH / ethanol / 1 h / Heating 5: 84 percent / HF (g) 6: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C View Scheme

1: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 2: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 3: KOH / ethanol / 1 h / Heating 4: 84 percent / HF (g) 5: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C View Scheme

1: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 2: KOH / ethanol / 1 h / Heating 3: 84 percent / HF (g) 4: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C View Scheme

1: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 2: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 3: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 4: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 5: KOH / ethanol / 1 h / Heating 6: 84 percent / HF (g) 7: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C View Scheme

palladium on activated charcoal T=310 - 320°C;