nickel in ethanol Heating;

1: 100 percent / K2CO3 / acetone / 45 °C 2: 1.) n-butyl lithium / 1.) THF, -78 deg C; 2.) from -78 deg C to room temperature 3: Raney nickel / ethanol / Heating View Scheme

1: 1.) n-butyl lithium / 1.) THF, -78 deg C; 2.) from -78 deg C to room temperature 2: Raney nickel / ethanol / Heating View Scheme

hydrogenchloride; n-butyllithium in tetrahydrofuran; hexane

1: 1.) n-butyllithium / 1.) hexane, THF, from -78 to -50 deg C, 2.) hexane, THF, from -78 to -4 deg C, 45 min 2: 52 percent / 3 N hydrochloric acid / diethyl ether 3: 95 percent / 1 N aq. sodium hydroxide / 1.) reflux, 2 h, 2.) ethanol, reflux, 45 min View Scheme