1: 81 percent / pyridinium p-toluenesulfonate (PPTS) / CH2Cl2 / Ambient temperature 2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, a) -78 deg C, 1 h, b) RT, 1 h 3: 1.) cuprous iodide / 1.) THF, ether, 0 deg C, 30 min, 2.) THF, ether, -78 deg C, 2 h 4: 95 percent / Amberlyst-15 resin (H+ form), methanol / 3 h / Ambient temperature View Scheme

1.1: morpholine; palladium(II) chloride bis(benzonitrile) complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C 2.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C 3.2: -78 - 20 °C 4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C 4.2: 2 h / 0 °C View Scheme

1: acetone; chromium (VI)-oxide; aqueous sulfuric acid 2: petroleum ether; manganese (II)-acetate; oxygen 3: copper (I)-chloride; ammonium chloride; aqueous acetone / Reagens 4: Sauerstoff 4: aqueous KOH-solution View Scheme