hydrogen; platinum(IV) oxide in ethanol 2 h; Heating;

1: 98 percent / p-toluenesulphonic acid / diethyl ether / 2 h / 0 °C 2: sodium amide / 18-crown-6-ether / 1.) xylene, reflux, 40 min. 2.) xylene, reflux, 8 h 3: p-toluenesulphonic acid / methanol / 1 h / Heating View Scheme

1: sodium amide / 18-crown-6-ether / 1.) xylene, reflux, 40 min. 2.) xylene, reflux, 8 h 2: p-toluenesulphonic acid / methanol / 1 h / Heating View Scheme

1: 75 percent / triphenylphosphine, pyridine, bromine / dioxane / 3 h / Ambient temperature 2: sodium amide / 18-crown-6-ether / 1.) xylene, reflux, 40 min. 2.) xylene, reflux, 8 h 3: p-toluenesulphonic acid / methanol / 1 h / Heating View Scheme

1: sodium amide / 18-crown-6-ether / 1.) xylene, reflux, 40 min. 2.) xylene, reflux, 8 h 2: p-toluenesulphonic acid / methanol / 1 h / Heating View Scheme

lithium aluminium tetrahydride in tetrahydrofuran; diethylene glycol dimethyl ether 10 h; Heating; Yield given. Title compound not separated from byproducts;