2: H2, quinoline / Pb, Pd, CaCO3 / light petroleum View Scheme

pyridine; phosphorus tribromide in diethyl ether 1.) overnight, 2.) reflux, 2 h;

1: H2, quinoline / Pd, Pb, CaCO3 / light petroleum View Scheme

1: 1.) ethylmagnesium bromide 2.) CuCl / 1.) THF, reflux, 6 h, 2.) reflux, 9 h 2: 66 percent / p-TsOH*H2O / methanol / 6 h / 55 °C 3: 92 percent / H2, quinoline / Lindlar's catalyst / hexane / 2070.2 Torr 4: 70 percent / PBr3, pyridine / diethyl ether / 1.) overnight, 2.) reflux, 2 h View Scheme

1: 92 percent / H2, quinoline / Lindlar's catalyst / hexane / 2070.2 Torr 2: 70 percent / PBr3, pyridine / diethyl ether / 1.) overnight, 2.) reflux, 2 h View Scheme

1: 66 percent / p-TsOH*H2O / methanol / 6 h / 55 °C 2: 92 percent / H2, quinoline / Lindlar's catalyst / hexane / 2070.2 Torr 3: 70 percent / PBr3, pyridine / diethyl ether / 1.) overnight, 2.) reflux, 2 h View Scheme

(i) EtMgBr, THF, (ii) /BRN= 1841105/, CuCN; Multistep reaction;