hydrogen; palladium on activated charcoal in methanol P=760 Torr; Ambient temperature;

1: CSA / CH2Cl2 / 15 °C 2: 70 percent / InCl3 / CH2Cl2 / 22 h / 0 °C 3: 70 percent / Bu3SnH; 1,1'-azobis(cyclohexane carbonitrile) / benzene / 16 h / Heating 4: H2 / Pd/C / methanol; ethyl acetate / 3 h / 20 °C View Scheme

magnesium in tetrahydrofuran 18 h; Ambient temperature;

1: 1.) tert-butyllithium / 1.) hexane, pentane, 0 deg C, 4.5h 2.) THF, 2h, 0-10 deg C 2: 92 percent / pyridine / 0.5 h / 100 - 110 °C 3: 87 percent / tetraethylammonium fluoride / tetrahydrofuran / 24 h / Ambient temperature 4: 83 percent / H2 / 10percent Pd/C / ethanol; ethyl acetate / 12 h / 760 Torr / Ambient temperature View Scheme

1: 95 percent / CH2Cl2 2: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate 3: 100 percent / aq. NaOH / methanol View Scheme