1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 17 h / -78 - 0 °C / Inert atmosphere 2.1: AlCl3, aluminium chloride; ethane-1,2-dithiol / nitromethane / 0.5 h / -20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11323294', constants.ctx, '0')">platinum(IV) oxide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=24&deg;C;&nbsp;1&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 &deg;C<br />1.2: 20 h / 0 - 24 &deg;C<br />2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 &deg;C<br />2.2: 1 h / 0 &deg;C<br />3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 2 h / 24 &deg;C / Reflux<br />4.1: toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.4 h / 24 - 50 &deg;C<br />5.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 1 h / 24 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 &deg;C<br />1.2: 1 h / 0 &deg;C<br />2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 2 h / 24 &deg;C / Reflux<br />3.1: toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.4 h / 24 - 50 &deg;C<br />4.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 1 h / 24 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 2 h / 24 &deg;C<br />2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 &deg;C<br />2.2: 20 h / 0 - 24 &deg;C<br />3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 &deg;C<br />3.2: 1 h / 0 &deg;C<br />4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 2 h / 24 &deg;C / Reflux<br />5.1: toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.4 h / 24 - 50 &deg;C<br />6.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 1 h / 24 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 2 h / 24 &deg;C / Reflux<br />2: toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.4 h / 24 - 50 &deg;C<br />3: platinum(IV) oxide; hydrogen / tetrahydrofuran / 1 h / 24 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1.1: potassium dihydrogenphosphate; Fremy’s salt / methanol; water / 1 h / 0 &deg;C<br />2.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 2 h / 24 &deg;C<br />3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 &deg;C<br />3.2: 20 h / 0 - 24 &deg;C<br />4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 &deg;C<br />4.2: 1 h / 0 &deg;C<br />5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 2 h / 24 &deg;C / Reflux<br />6.1: toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.4 h / 24 - 50 &deg;C<br />7.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 1 h / 24 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1.1: pyridinium p-toluenesulfonate / toluene / Reflux<br />1.2: 1.83 h<br />2.1: potassium dihydrogenphosphate; Fremy’s salt / methanol; water / 1 h / 0 &deg;C<br />3.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 2 h / 24 &deg;C<br />4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 &deg;C<br />4.2: 20 h / 0 - 24 &deg;C<br />5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 &deg;C<br />5.2: 1 h / 0 &deg;C<br />6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 2 h / 24 &deg;C / Reflux<br />7.1: toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.4 h / 24 - 50 &deg;C<br />8.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 1 h / 24 &deg;C<br /> <br /> &nbsp;