1.1: caesium carbonate / methanol / pH 7 1.2: 11 h / 0 - 20 °C / Inert atmosphere 2.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 0 - 20 °C 3.1: toluene / 5 h / 60 °C / Inert atmosphere 4.1: 10 Pd(OH)2 on C; hydrogen / methanol / 36 h / 20 °C 5.1: piperidine; 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 192 h / 20 °C / Inert atmosphere View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '8128150', constants.ctx, '0')">sodium hydroxide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=20&deg;C;&nbsp;0.75&nbsp;h;&nbsp;<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 0 - 20 &deg;C / Inert atmosphere<br />2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 &deg;C / Inert atmosphere<br />2.2: 13.5 h / 0 - 60 &deg;C / Inert atmosphere<br />3.1: water; sodium hydroxide / tetrahydrofuran / 0.75 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; toluene / 12 h / Reflux<br />2.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 0 - 20 &deg;C / Inert atmosphere<br />3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 &deg;C / Inert atmosphere<br />3.2: 13.5 h / 0 - 60 &deg;C / Inert atmosphere<br />4.1: water; sodium hydroxide / tetrahydrofuran / 0.75 h / 20 &deg;C<br /> <br /> &nbsp;