1: 76.6 percent / DIEA / CH2Cl2 / 3 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 0 deg C, 1.5 h, 2.) DMF, 40 deg C, 12 h 3: 76.8 percent / H2, HCl / Raney Ni / ethanol / 1.5 h / Ambient temperature 4: 75 percent / DMAP / pyridine / 2 h / 0 °C 5: Tl2CO3, Pd<P(C6H5)3>4 / benzene / 23 h / Ambient temperature 6: nBuNF, HMPA, 4 Angstroem molecular sieves / tetrahydrofuran / 8 h / Ambient temperature 7: MnO2 / CH2Cl2 / 1 h / Heating View Scheme

hydrogenchloride; N-chloro-succinimide; dibenzoyl peroxide in acetic acid; acetonitrile Chlorination; 6.5 h; Heating;

1: thionyl chloride / dichloromethane / 20 h / 0 - 26 °C 2: dimethyl sulfoxide / 2.25 h / 0 - 10 °C 3: dimethylsulfide borane complex / tetrahydrofuran / 21 h / 0 - 20 °C / Reflux View Scheme