4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane Product distribution / selectivity;

1: copper(l) iodide / tetrahydrofuran / -78 - 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h 3: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -60 - -50 °C 4: sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol View Scheme

1: copper(l) iodide / tetrahydrofuran / -78 - 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h 3: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -60 - -50 °C View Scheme