1: 92 percent / Et3N / CH2Cl2 / 2 h / 20 °C 2: 95 percent / LiAlH4 / diethyl ether / 16 h / 20 °C 3: 97 percent / D2 / RhCl(PPh3)3 / benzene / 36 h 4: 89 percent / aq. HCl / methanol / 24 h / 20 °C 5: IBX / dimethylsulfoxide / 12 h / 20 °C 6: 88 mg / H2SO4; CrO3 / acetone; H2O View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11460447', constants.ctx, '0')">lithium aluminium tetrahydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a> <br />T=20&deg;C;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 85 percent / NBS; PPh₃ / dimethylformamide / 1 h / 0 &deg;C<br />2: 73 percent / BuLi / tetrahydrofuran; hexane / -78 - 20 &deg;C<br />3: NBS / acetone; H₂O / 0.02 h / -30 &deg;C<br />4: 97 percent / LiAlH₄ / diethyl ether / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 73 percent / BuLi / tetrahydrofuran; hexane / -78 - 20 &deg;C<br />2: NBS / acetone; H₂O / 0.02 h / -30 &deg;C<br />3: 97 percent / LiAlH₄ / diethyl ether / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 69 percent / HMPA; BuLi / tetrahydrofuran; hexane / -15 - 0 &deg;C<br />2: 85 percent / NBS; PPh₃ / dimethylformamide / 1 h / 0 &deg;C<br />3: 73 percent / BuLi / tetrahydrofuran; hexane / -78 - 20 &deg;C<br />4: NBS / acetone; H₂O / 0.02 h / -30 &deg;C<br />5: 97 percent / LiAlH₄ / diethyl ether / 20 &deg;C<br /> <br /> &nbsp;