pyridine; thionyl chloride 24 h; Heating;

1: oxoammonium salt; silica gel / dichloromethane / 24 h / 20 °C / |Acidic conditions 2: oxoammonium salt; 2,6-dimethylpyridine / dichloromethane / 20 °C / |Sealed tube View Scheme

Stage #1: &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0&deg;C;&nbsp;0.166667&nbsp;h;&nbsp;&nbsp;Inert atmosphereSealed tube;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3570522', constants.ctx, '0')">tetrabutyl ammonium fluoride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0 - 20&deg;C;&nbsp;&nbsp;Inert atmosphereSealed tube;&nbsp;<br />Stage #3: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3570522', constants.ctx, '0')">tetrabutyl ammonium fluoride</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0 - 20&deg;C;&nbsp;&nbsp;Inert atmosphereSealed tube;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: sodium tetrahydroborate / methanol / 1 h / 20 &deg;C<br />2.1: tetrahydrofuran / 0.17 h / 0 &deg;C / |Inert atmosphere; |Sealed tube<br />2.2: 0 - 20 &deg;C / |Inert atmosphere; |Sealed tube<br />2.3: 0 - 20 &deg;C / |Inert atmosphere; |Sealed tube<br /> <br /> &nbsp;