sulfuric acid in acetone T=20°C;

acetic acid; zinc 2.) r.t., 1 h;

1: 1.) lithamide in liq. ammonia / 1.) 2 h, 2.) ether, 20 deg C, 20 min 2: 1.) diborane, 3.) hydrogen peroxide, 3M sodium hydroxide / 1.) diglyme, THF, 0 deg C, 2 h, 2.) THF, 10 deg C, 2 h, 20 deg C, 2 h, 3.) water, 0 deg C, 20 min 3: 55 percent / sulphuric acid / acetone / 20 °C View Scheme

1: 1.) diborane, 3.) hydrogen peroxide, 3M sodium hydroxide / 1.) diglyme, THF, 0 deg C, 2 h, 2.) THF, 10 deg C, 2 h, 20 deg C, 2 h, 3.) water, 0 deg C, 20 min 2: 55 percent / sulphuric acid / acetone / 20 °C View Scheme