tin(IV) chloride; acetyl chloride Ambient temperature;

1: 1.) EtMgBr / 2.) CuCl / 1.) THF, 50 deg C, 30 min; 2.) THF, 50-55 deg C, 2 h 2: 82 percent / acetyl chloride, stannic chloride / CH2Cl2 / 0.25 h / 10 - 15 °C View Scheme

1: 1.) EtMgBr / 2.) CuCl / 1.) THF, 50 deg C, 30 min; 2.) THF, 50-55 deg C, 2 h 2: 82 percent / acetyl chloride, stannic chloride / CH2Cl2 / 0.25 h / 10 - 15 °C View Scheme

1: 1.) n-butyllithium; 2.) mercurous chloride, cuprous chloride / 1.) hexane, THF, -78 deg C, 1 h; 2.) hexane, THF, -78 deg C --> room temp., then reflux, 5.5 h 2: 1.) EtMgBr / 2.) CuCl / 1.) THF, 50 deg C, 30 min; 2.) THF, 50-55 deg C, 2 h 3: 82 percent / acetyl chloride, stannic chloride / CH2Cl2 / 0.25 h / 10 - 15 °C View Scheme

hydrogenchloride in diethyl ether