1: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 2: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 3: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 4: Mg / tetrahydrofuran / 20 h / Heating 5: CuI / tetrahydrofuran / 0.5 h / -3 °C View Scheme

1: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 2: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 3: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 4: Mg / tetrahydrofuran / 20 h / Heating 5: CuI / tetrahydrofuran / 0.5 h / -3 °C 6: 35 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

hydrogen; palladium on activated charcoal in ethanol P=2585.7 Torr; 13 h;

1: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 2: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C View Scheme

1: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 2: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 3: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min View Scheme

1: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 2: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 3: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 4: Mg / tetrahydrofuran / 20 h / Heating 5: CuI / tetrahydrofuran / 0.5 h / -3 °C View Scheme

1: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 2: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 3: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 4: Mg / tetrahydrofuran / 20 h / Heating 5: CuI / tetrahydrofuran / 0.5 h / -3 °C 6: 62 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

1: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 2: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 3: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 4: Mg / tetrahydrofuran / 20 h / Heating 5: CuI / tetrahydrofuran / 0.5 h / -3 °C 6: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 7: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme