potassium hydroxide 5 h; Heating;

1: 80 percent / KOH / methanol / Heating 2: 97 percent / LiAlH4 / diethyl ether 3: 76 percent / CBr4, PPh3 / CH2Cl2 View Scheme

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3535167', constants.ctx, '0')">lithium cyanide</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;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '13159932', constants.ctx, '0')">samarium diiodide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '906698', constants.ctx, '0')"><i>tert</i>-butyl alcohol</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;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: (CH₃(CH₃)3)3P; CCl₄ / acetonitrile / 1 h / 0 &deg;C<br />2: 18-crown-16 / acetonitrile / 12 h / 70 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: lithium aluminium hydride<br />2: 1.) thionyl chloride / 1.) diethyl ether, 2.) DMF, 90 deg C, 4 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: lithium aluminum hydride / tetrahydrofuran / 0.5 h / 0 &deg;C<br />2: triethylamine / CH₂Cl₂ / 1 h / 20 &deg;C<br />3: dimethylformamide / 20 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209273', constants.ctx, '0')">thionyl chloride</a> <br />&nbsp;1.) diethyl ether, 2.) DMF, 90 deg C, 4 h;&nbsp;&nbsp;Multistep reaction;&nbsp;<br /> &nbsp;