1: NaOEt / ethanol / 1.) 10 deg C, 1 h, 2.) room temp, 1 h 2: xylene / 0.5 h / Heating 3: 34 percent / Raney Ni / tetrahydrofuran / 0.17 h / Heating View Scheme

1: NaOEt / ethanol / 1.) 10 deg C, 1 h, 2.) room temp, 1 h 2: xylene / 0.5 h / Heating 3: 34 percent / Raney Ni / tetrahydrofuran / 0.17 h / Heating 4: 60 percent / H2, HCl / 10percent Pd-C / ethyl acetate; methanol / 5 h / Ambient temperature View Scheme

1: NaOEt / ethanol / 1.) 10 deg C, 1 h, 2.) room temp, 1 h 2: xylene / 0.5 h / Heating 3: 34 percent / Raney Ni / tetrahydrofuran / 0.17 h / Heating 4: 60 percent / H2, HCl / 10percent Pd-C / ethyl acetate; methanol / 5 h / Ambient temperature 5: 70 percent / 40percent HBr-AcOH / 1 h / 40 °C View Scheme