hydrogenchloride; sodium hydroxide in tetrahydrofuran; ethyl acetate

1: DMAP / tetrahydrofuran / Ambient temperature 2: 1,4-dicyanonaphthalene, methyl viologen / acetonitrile / 10 h / Irradiation 3: TiCl4 / CH2Cl2 / 4 h / -78 °C 4: 82 percent / Li / liquid ammonia; tetrahydrofuran / 1 h / -33 °C 5: K2CO3 / tetrahydrofuran; H2O View Scheme

1: DMAP / tetrahydrofuran / Ambient temperature 2: 1,4-dicyanonaphthalene, methyl viologen / acetonitrile / 10 h / Irradiation 3: TiCl4 / CH2Cl2 / 4 h / -78 °C 4: 82 percent / Li / liquid ammonia; tetrahydrofuran / 1 h / -33 °C 5: K2CO3 / tetrahydrofuran; H2O 6: H2 / Pd/C / ethanol / 10 h View Scheme

1: DMAP / tetrahydrofuran / Ambient temperature 2: 1,4-dicyanonaphthalene, methyl viologen / acetonitrile / 10 h / Irradiation 3: TiCl4 / CH2Cl2 / 4 h / -78 °C 4: 82 percent / Li / liquid ammonia; tetrahydrofuran / 1 h / -33 °C 5: K2CO3 / tetrahydrofuran; H2O 6: H2 / Pd/C / ethanol / 10 h View Scheme