hydrogen; 10 palladium on active carbon in methanol P=760 Torr; 2 h; Ambient temperature;

1: With water; nickel in ethanol 1.5 h; Heating; 2: With hydrogen; acetic acid; palladium on activated charcoal in methanol T=50°C; P=15200 Torr; 2 h;

1: 77.9 g / aq.K2CO3 / tetrahydrofuran / 0.25 h / 0 °C 2: 78.4 g / aq.(CrO3/H2SO4) / acetone / 3 h / -5 °C 3: 86.3 percent / H2 / 10percentPd/C / methanol / 2 h / 760 Torr / Ambient temperature View Scheme

1: 1.) LDA, / 1.) THF, -78 deg C, 30 min, 2.) THF, -20 deg C, 20 min 2: 100 percent / LAH / tetrahydrofuran / 1 h / Heating 3: 65 percent / H2 / 10percentPd/C / ethyl acetate; acetic acid / 2 h / 2327.2 Torr 4: 77.9 g / aq.K2CO3 / tetrahydrofuran / 0.25 h / 0 °C 5: 78.4 g / aq.(CrO3/H2SO4) / acetone / 3 h / -5 °C 6: 86.3 percent / H2 / 10percentPd/C / methanol / 2 h / 760 Torr / Ambient temperature View Scheme

1: 86 percent / TosOH / toluene / 9 h / Heating 2: 1.) LDA, / 1.) THF, -78 deg C, 30 min, 2.) THF, -20 deg C, 20 min 3: 100 percent / LAH / tetrahydrofuran / 1 h / Heating 4: 65 percent / H2 / 10percentPd/C / ethyl acetate; acetic acid / 2 h / 2327.2 Torr 5: 77.9 g / aq.K2CO3 / tetrahydrofuran / 0.25 h / 0 °C 6: 78.4 g / aq.(CrO3/H2SO4) / acetone / 3 h / -5 °C 7: 86.3 percent / H2 / 10percentPd/C / methanol / 2 h / 760 Torr / Ambient temperature View Scheme

1.1: hexamethyldisilazane; n-butyllithium / tetrahydrofuran / 1 h / -10 °C 1.2: 19 g / tetrahydrofuran / 4 h / -10 - 20 °C 2.1: 10.2 g / H2 / 10 percent Pd/C / ethyl acetate / 2 h / 20 °C / 760 Torr 3.1: triethylamine / tetrahydrofuran / 6 h / Heating 4.1: 2.96 g / Lawesson's reagent / toluene / 5 h / 100 °C 5.1: Raney-Ni; water / ethanol / 1.5 h / Heating 5.2: 35 percent / hydrogen; glacial acetic acid / 10 percent Pd/C / methanol / 2 h / 50 °C / 15200 Torr View Scheme

1.1: triethylamine / tetrahydrofuran / 6 h / Heating 2.1: 2.96 g / Lawesson's reagent / toluene / 5 h / 100 °C 3.1: Raney-Ni; water / ethanol / 1.5 h / Heating 3.2: 35 percent / hydrogen; glacial acetic acid / 10 percent Pd/C / methanol / 2 h / 50 °C / 15200 Torr View Scheme

1.1: 2.96 g / Lawesson's reagent / toluene / 5 h / 100 °C 2.1: Raney-Ni; water / ethanol / 1.5 h / Heating 2.2: 35 percent / hydrogen; glacial acetic acid / 10 percent Pd/C / methanol / 2 h / 50 °C / 15200 Torr View Scheme

1: carbonyldiimidazole, Et3N / acetonitrile / 48 h / Ambient temperature 2: bromotrimethylsilane / CH2Cl2 View Scheme