hydrogen; 5 Pd(II)/C(eggshell); triethylamine in tetrahydrofuran; ethanol T=35°C; P=4500.45 - 5250.53 Torr; 24 h;

1.1: hydrogen / triethylamine; 5 Pd(II)/C(eggshell) / ethanol; tetrahydrofuran / 24 h / 35 °C / 4500.45 - 5250.53 Torr 2.1: sodium methylate / tetrahydrofuran / 1 h / 20 °C 2.2: 2.25 h / 20 °C View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1.1: potassium carbonate / acetone / 5 h / Reflux<br />2.1: <i>N</i>,<i>N</i>-dimethyl-aniline / Inert atmosphere; Reflux<br />2.2: 25 &deg;C<br />3.1: ozone / dichloromethane / -78 - 20 &deg;C / Inert atmosphere<br />3.2: 20 &deg;C<br />4.1: toluene-4-sulfonic acid / toluene / 0.75 h / Reflux<br /> <br /> &nbsp;