1: SnCl2 2: 81 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C 3: 71 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4: 88 percent / Pd(PPh3)4; pyrrolidine; PPh3 / CH2Cl2 / 0.17 h / 20 °C 5: 28 percent / 1,4-cyclohexadiene / Pd/C / ethanol / 4 h / 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11536633', constants.ctx, '0')">lithium borohydride</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;2.5&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: 92 percent / K₂CO₃ / acetone / 24 h / Heating<br />2.1: 78 percent / SnCl₄; HNO₃ / CH₂Cl₂ / 0.08 h / -78 &deg;C<br />3.1: 83 percent / LiOH / tetrahydrofuran; H₂O; methanol / 12 h / 20 &deg;C<br />4.1: thionyl chloride; DMF / benzene / 6 h<br />4.2: 85 percent / Et₃N / tetrahydrofuran / 0 - 20 &deg;C<br />5.1: 85 percent / LiBH₄ / tetrahydrofuran / 2.5 h / 0 - 20 &deg;C<br /> <br /> &nbsp;