sodium in diethyl ether; ammonia; toluene T=-78°C;

1: 1.) 1.2 M methyllithium / 1.) tetrahydrofuran, diethyl ether, 0 deg C; 2.) diethyl ether, r.t. 2: 65 percent / sodium / toluene; liquid ammonia; diethyl ether / -78 °C View Scheme