Na in toluene at about 100°C; very exothermic react.;;

sodium in decane 3 h; Heating;

Multistep reaction;

48 h; Heating;

hydrogenchloride 0.5 h; Heating; Yield given;

1: conc. HCl / 0.5 h / Heating 2: 1) oxalyl chloride, DMSO; 2) Et3N / CH2Cl2; 1) -60 deg C, 15 min View Scheme

1: conc. HCl / 0.5 h / Heating 2: 1) oxalyl chloride, DMSO; 2) Et3N / CH2Cl2; 1) -60 deg C, 15 min 3: 50 percent / Hexamethyldisilazane / petroleum ether / 1) -20 deg C, 20 min; 2) room temp., 2.5 h 4: 76.4 percent / diethyl ether / -80 °C 5: 80 percent / diethyl ether / 1) -95 deg C, 2.5 h; 2) -60 deg C, 0.5 h 6: 100 percent / N,N'-carbonyldiimidazole / toluene / 3 h / Heating; or with methanseulfonyl chloride, Et3N at room temp. View Scheme