hydrogen; palladium on activated charcoal in ethanol

hydrogen; palladium on activated charcoal in ethanol 20 h;

1: 1.) n-BuLi / 1.) n-hexane - THF, -30 deg C, 20 min, 2.) 17 h, temperature gradually warmed to room temperature 2: 80 percent / pyridinium tosylate / H2O / acetone / 4 h / Heating 3: 1.) n-BuLi / 1.) n-hexane - THF, -70 deg C, 20 min, 2.) 17 h, temperature gradually warmed to room temperature 4: 95 percent / hydrogen / 5percent Pd/C / ethanol / 20 h View Scheme

1: 1.) n-BuLi / 1.) n-hexane - THF, -30 deg C, 20 min, 2.) 17 h, temperature gradually warmed to room temperature 2: 80 percent / pyridinium tosylate / H2O / acetone / 4 h / Heating 3: 1.) n-BuLi / 1.) n-hexane - THF, -70 deg C, 20 min, 2.) 17 h, temperature gradually warmed to room temperature 4: 95 percent / hydrogen / 5percent Pd/C / ethanol / 20 h View Scheme

1: 1.) n-BuLi / 1.) n-hexane - THF, -70 deg C, 20 min, 2.) 17 h, temperature gradually warmed to room temperature 2: 95 percent / hydrogen / 5percent Pd/C / ethanol / 20 h View Scheme

1: 80 percent / pyridinium tosylate / H2O / acetone / 4 h / Heating 2: 1.) n-BuLi / 1.) n-hexane - THF, -70 deg C, 20 min, 2.) 17 h, temperature gradually warmed to room temperature 3: 95 percent / hydrogen / 5percent Pd/C / ethanol / 20 h View Scheme

1: 87 percent / TosOH / diethyl ether / 20 h / Ambient temperature 2: 1) Mg, CuI / 1) THF, 0.5 h, 2) -10 deg C, 4 h, then room temperature, 4 h 3: TosOH / methanol / 15 h / Ambient temperature 4: 87 percent / pyridine 5: 1) Mg, CuI / 1) THF, -15 deg C, 0.5 h, 2) -10 deg C, 4 h, then room temperature, 4 h 6: 95 percent / H2 / 5percent Pd-C / ethanol View Scheme

1: 1) Mg, CuI / 1) THF, 0.5 h, 2) -10 deg C, 4 h, then room temperature, 4 h 2: TosOH / methanol / 15 h / Ambient temperature 3: 87 percent / pyridine 4: 1) Mg, CuI / 1) THF, -15 deg C, 0.5 h, 2) -10 deg C, 4 h, then room temperature, 4 h 5: 95 percent / H2 / 5percent Pd-C / ethanol View Scheme