hydrogen; palladium on activated charcoal in ethanol P=2327.2 Torr; 3 h;

in tetrahydrofuran

diisobutylaluminium hydride in toluene 1.) -70 deg C, 1 h, 2.) RT, 12 h;

diisobutylaluminium hydride in toluene 1.) -70 deg C, 1 h, 2.) RT, 12 h;

1: 1.) LDA / 1.) THF, hexanes, -70 to -60 deg C, 15 min, 2.) THF, hexanes, a) -70 to -60 deg C, 1 h, b) RT, 1 h 2: 94 percent / NaI / butan-2-one / 12 h / Heating 3: 75 percent / i-Bu2AlH / toluene / 1.) -70 deg C, 1 h, 2.) RT, 12 h View Scheme

1: 91 percent / p-toluene sulfonic acid / benzene / 3 h / Heating 2: LiAlH4 / tetrahydrofuran / 3 h / Heating 3: 10percent aq. HCl / 1 h / Ambient temperature 4: 10percent aq. NaOH / 1 h / Ambient temperature; pH = 9 View Scheme

1: 46 percent / 40percent benzyltrimethylammonium hydroxide in MeOH / dioxane / 0 - 20 °C 2: 91 percent / p-toluene sulfonic acid / benzene / 3 h / Heating 3: LiAlH4 / tetrahydrofuran / 3 h / Heating 4: 10percent aq. HCl / 1 h / Ambient temperature 5: 10percent aq. NaOH / 1 h / Ambient temperature; pH = 9 View Scheme

1: 10percent aq. HCl / 1 h / Ambient temperature 2: 10percent aq. NaOH / 1 h / Ambient temperature; pH = 9 View Scheme