1: 60 percent / LiAlH4 / tetrahydrofuran / -10 °C 2: N-bromosuccinimide (NBS) / CHCl3 / 0.17 h / Ambient temperature 3: H2, Et3N / 10percent Pd/C / methanol / 0.33 h / Ambient temperature View Scheme

hydrogen; palladium on activated charcoal

1: 67 percent / lithium dicyclohexylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / Ambient temperature 2: 78 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / benzene / 1 h / Heating 3: 36 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature 4: 59 percent / Amberlyst A15 resin (H(1+) form) / CH2Cl2 / 10 h / Ambient temperature View Scheme

1: 78 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / benzene / 1 h / Heating 2: 36 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature 3: 59 percent / Amberlyst A15 resin (H(1+) form) / CH2Cl2 / 10 h / Ambient temperature View Scheme

1: 36 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature 2: 59 percent / Amberlyst A15 resin (H(1+) form) / CH2Cl2 / 10 h / Ambient temperature View Scheme

1: 72 percent / nitromethane / 48 h / Ambient temperature 2: 67 percent / lithium dicyclohexylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / Ambient temperature 3: 78 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / benzene / 1 h / Heating 4: 36 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature 5: 59 percent / Amberlyst A15 resin (H(1+) form) / CH2Cl2 / 10 h / Ambient temperature View Scheme

N-bromosuccinmide; water in chloroform 3 h; Ambient temperature;