1: 93.6 percent / H2 / Pt / methanol / 0 °C / 750.06 Torr 2: 100 percent / p-toluenesulphonic acid monohydrate / tetrahydrofuran; acetic acid; H2O / 7 h / Heating 3: 82.1 percent / 48percent HBr / acetic acid / 28 h / 122 - 123 °C 4: 51.2 percent / BuLi / hexamethylphosphoric acid triamide / 20 h / 0 °C 5: 95 percent / p-toluenesulphonic acid monohydrate / tetrahydrofuran; acetic acid; H2O / 6 h / Heating 6: H2, quinoline / Lindlar's catalyst / ethyl acetate / 37 °C View Scheme

1: 93.6 percent / H2 / Pt / methanol / 0 °C / 750.06 Torr 2: 100 percent / p-toluenesulphonic acid monohydrate / tetrahydrofuran; acetic acid; H2O / 7 h / Heating View Scheme