1: 85 percent / LiAlH4, AlCl3 / tetrahydrofuran / 1 h / -78 °C 2: 90 percent / methanol / 15 h / Ambient temperature 3: NaH / dioxane; dimethylformamide / 6 h / Heating View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1708400', constants.ctx, '0')">2,2'-azo-bisisobutyronitrile</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587329', constants.ctx, '0')">tri-n-butyl-tin hydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '969212', constants.ctx, '0')">benzene</a> <br />&nbsp;Heating;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 82.8 percent / pyridinium tosylate / benzene / 14 h / Heating<br />2: 80 percent / NaI / acetone / 1 h / 50 &deg;C<br />3: 22 percent / Bu₃SnH, AIBN / benzene / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 80 percent / NaI / acetone / 1 h / 50 &deg;C<br />2: 22 percent / Bu₃SnH, AIBN / benzene / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 90 percent / 2N NaOH / H₂O / Ambient temperature; pH ca. 7<br />2: 82.8 percent / pyridinium tosylate / benzene / 14 h / Heating<br />3: 80 percent / NaI / acetone / 1 h / 50 &deg;C<br />4: 22 percent / Bu₃SnH, AIBN / benzene / Heating<br /> <br /> &nbsp;