trifluorormethanesulfonic acid in 1,2-dichloro-ethane 18 h; Reflux;

quinoline; hydrogen; Lindlar's catalyst in n-heptane T=0°C; 6 h;

2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene in water; acetonitrile T=20°C; 7 h;

1: 1.) EtMgBr / 1) ether, overnight; 2) reflux, 1 h 2: 74 percent / PBr3, pyridine / diethyl ether / -20 - 20 °C 3: 1.) sodium / 1) EtOH; 2) EtOH, 2 h 4: 85 percent / KOH, H2O / ethanol / 4 h / Heating 5: 82 percent / 4 h / 180 °C 6: 97 percent / H2, quinoline / Lindlar catalyst / heptane / 6 h / 0 °C View Scheme

1: 74 percent / PBr3, pyridine / diethyl ether / -20 - 20 °C 2: 1.) sodium / 1) EtOH; 2) EtOH, 2 h 3: 85 percent / KOH, H2O / ethanol / 4 h / Heating 4: 82 percent / 4 h / 180 °C 5: 97 percent / H2, quinoline / Lindlar catalyst / heptane / 6 h / 0 °C View Scheme

1: 1.) sodium / 1) EtOH; 2) EtOH, 2 h 2: 85 percent / KOH, H2O / ethanol / 4 h / Heating 3: 82 percent / 4 h / 180 °C 4: 97 percent / H2, quinoline / Lindlar catalyst / heptane / 6 h / 0 °C View Scheme

1: 85 percent / KOH, H2O / ethanol / 4 h / Heating 2: 82 percent / 4 h / 180 °C 3: 97 percent / H2, quinoline / Lindlar catalyst / heptane / 6 h / 0 °C View Scheme

1: tetrahydrofuran; hexane / -42 - 20 °C / Inert atmosphere 2: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; acetonitrile / 7 h / 20 °C View Scheme

1: diisobutylaluminium hydride / hexanes; dichloromethane / -78 °C / Inert atmosphere 2: tetrahydrofuran; hexane / -42 - 20 °C / Inert atmosphere 3: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; acetonitrile / 7 h / 20 °C View Scheme