n-butyllithium; copper(I) bromide; lithium bromide in tetrahydrofuran; hexane T=0°C;

hydrogenchloride in acetone 0.5 h;

1: 50 percent / BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 5 min, 2.) -78 deg C, 5 min 2: 80 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / Ambient temperature 3: 75 percent / 37percent aq. HCl / acetone / 0.5 h View Scheme

1: 50 percent / BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 5 min, 2.) -78 deg C, 5 min 2: 80 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / Ambient temperature 3: 75 percent / 37percent aq. HCl / acetone / 0.5 h View Scheme

1: 80 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / Ambient temperature 2: 75 percent / 37percent aq. HCl / acetone / 0.5 h View Scheme

Yield given. Multistep reaction;