n-butyllithium in hexane T=-78 - -20°C; Wittig Rearrangement; 8 h; Inert atmosphere;

n-butyllithium in tetrahydrofuran T=-78 - -20°C; Wittig Rearrangement; 8 h; Inert atmosphere; TemperatureTime;

1: 93 percent / H2 / Adams catalyst / ethyl acetate / 1.33 h / 760 Torr 2: 1.) HCl, 2.) zinc powder, acetic acid / 1.) EtOH, reflux, 2 d, 2.) reflux 3: LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 0.5 h; Ambient temperature; Yield given;

1: 1.) HCl, 2.) zinc powder, acetic acid / 1.) EtOH, reflux, 2 d, 2.) reflux 2: LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme