1: With palladium 10 on activated carbon; hydrogen in ethanol T=20°C; 6 h; 2: With ammonium cerium (IV) nitrate in water; acetonitrile T=0°C; 1 h; Inert atmosphere;

1: H2 / Pd/C / ethanol / 5 h / 20 °C 2: cerric ammonium nitrate / acetonitrile; H2O / 1 h / 0 °C View Scheme

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3596973', constants.ctx, '0')">lithium perchlorate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '747939', constants.ctx, '0')">2,3-dicyano-5,6-dichloro-p-benzoquinone</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br /> <br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098214', constants.ctx, '0')">hydrogenchloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '505945', constants.ctx, '0')">ethylene glycol</a> <br />T=60&deg;C;&nbsp;3&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1.1: tetrahydrofuran / 1 h / 10 &deg;C<br />2.1: N,N-dimethyl-formamide / 3 h / 20 &deg;C / |Inert atmosphere<br />3.1: potassium carbonate / tetrahydrofuran / 24 h / 20 &deg;C / |Inert atmosphere<br />3.2: 24 h / |Reflux; |Inert atmosphere<br />4.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / |Inert atmosphere; |Reflux<br />5.1: tetra(n-butyl)ammonium dichromate(VI) / chloroform / 10 h / |Inert atmosphere; |Reflux<br />6.1: boron tribromide / dichloromethane / 0.08 h / 0 &deg;C / |Inert atmosphere<br />7.1: sodium hydroxide / water; dimethyl sulfoxide / 3 h / 20 &deg;C / |Inert atmosphere<br /> <br /> &nbsp;