tin(IV) chloride; acetyl chloride Ambient temperature;

ethylmagnesium bromide; copper(l) chloride

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 View Scheme

potassium hydroxide in methanol T=0°C; 16 h;

1: 80 percent / potassium hydroxide / methanol / 16 h / 0 °C 2: 1.) EtMgBr / 2.) CuCl / 1.) THF, 50 deg C, 30 min; 2.) THF, 50-55 deg C, 2 h 3: 77 percent / potassium hydroxide / methanol / 16 h / 0 °C View Scheme