1: 1.) ethylmagnesium bromide, copper(I) bromide / 1.) THF, -78 -> 25 deg C, 2.) -78 -> 25 deg C 2: H2 / Lindlar catalyst / hexane / 25 °C 3: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 4: 88 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 25 °C 5: 80 percent / p-toluenesulfonic acid / ethanol / 45 °C 6: 75 percent / H2, quinoline / Lindlar catalyst / hexane / 1.5 h / 25 °C / 760 Torr 7: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

hydrogenchloride in methanol

in Petroleum ether T=20 - 25°C; 72 h;

hydrogenchloride 1.) ether, 0 deg C;

hydrogenchloride; lithium amide; ammonia -33 deg C; Yield given. Multistep reaction;

2: 1.) H2, 2.) CBr3, Ph3P / 1.) Lindlar / 1.) CH2Cl2, 25 deg C, 2.) CH2Cl2, 0 deg C View Scheme

Yield given. Multistep reaction;

2: 1.) H2, 2.) CBr3, Ph3P / 1.) Lindlar / 1.) CH2Cl2, 25 deg C, 2.) CH2Cl2, 0 deg C View Scheme

View Scheme

1: 1.) LiNH2/NH3, 2.) 1N HCl / -33 deg C 2: 8N Jones reagent / 0 °C 3: oxalylchloride/DMF, 1drop / benzene / 1 h View Scheme