1: liquid ammonia; methanol / -190 °C / anschliessendes Erhitzen auf 140grad und Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin 2: hydrogen chloride; methanol / Erhitzen des Reaktionsprodukts mit Acetanhydrid und Natriumacetat 3: aqueous hydrochloric acid View Scheme

bis(η5-cyclopentadienyl)titanium dichloride in tetrahydrofuran

bis(η5-cyclopentadienyl)titanium dichloride in tetrahydrofuran

1: 1.) NaOH / 1.) H2O, reflux, 48 h, 2.) DMSO, RT, 3 h 2: 100 percent / 80percent aq. HOAc / 0.5 h / 80 °C 3: 74 percent / diethyl azodicarboxylate, triphenylphosphine, CH3I / tetrahydrofuran / 19 h / Ambient temperature 4: DBU / toluene / 23 h / 80 °C 5: Amberlite IR 120 B resin / tetrahydrofuran; H2O / 22 h / Ambient temperature 6: 77 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2.5 h / Ambient temperature 7: 46 percent / H2 / Pd(OH)2/C / ethyl acetate / 0.5 h / 760 Torr / Ambient temperature 8: 96 percent / pyridine / Ambient temperature 9: 86 percent / trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 8 h / -5 °C 10: 66 percent / ceric ammonium nitrate / acetonitrile; H2O / 14 h / 5 °C 11: 94 percent / CH2Cl2 / 14 h / Ambient temperature 12: 1.) 1M aq. NaOH, 2.) pyridine / 1.) MeOH, 50 deg C, overnight, 2.) overnight 13: 1.) diethyl cyanophosphonate, NEt3, 2.) pyridine / 1.) DMF, 0 deg C, 2.5 h, 2.) RT, 2 h 14: 94 percent / NaOMe / methanol / 0.5 h / 0 °C 15: 45 percent / trifluoroacetic acid / H2O / 1 h / Ambient temperature View Scheme