1: 87 percent / 1 h / Heating 2: 13 percent / copper bronze / dimethylformamide / 16 h / 170 °C View Scheme

thionyl chloride; N-benzyl-N,N,N-triethylammonium chloride T=140°C; 3 h;

pyridine; thionyl chloride in chlorobenzene 96 h; Heating;

1: 75 percent / lithium aluminum hydride / diethyl ether / 3 h / Heating 2: 78 percent / chromium trioxide-pyridine complex / pyridine / 2 h / Ambient temperature View Scheme

1: 75 percent / lithium aluminum hydride / diethyl ether / 3 h / Heating 2: 78 percent / chromium trioxide-pyridine complex / pyridine / 2 h / Ambient temperature 3: 1.) sodium hydride / 1.) DMSO, R.T., 20 min, 2.) R.T. 4 h. View Scheme

1: 75 percent / lithium aluminum hydride / diethyl ether / 3 h / Heating 2: 78 percent / chromium trioxide-pyridine complex / pyridine / 2 h / Ambient temperature 3: 1.) sodium hydride / 1.) DMSO, R.T., 20 min, 2.) R.T. 4 h. 4: 34 percent / triethylamine / benzene / 6 h / Irradiation View Scheme