1: 73 percent / BuLi / tetrahydrofuran; hexane / -78 - 20 °C 2: NBS / acetone; H2O / 0.02 h / -30 °C 3: 97 percent / LiAlH4 / diethyl ether / 20 °C 4: 92 percent / Et3N / CH2Cl2 / 2 h / 20 °C 5: 95 percent / LiAlH4 / diethyl ether / 16 h / 20 °C 6: 97 percent / D2 / RhCl(PPh3)3 / benzene / 36 h 7: 89 percent / aq. HCl / methanol / 24 h / 20 °C 8: IBX / dimethylsulfoxide / 12 h / 20 °C 9: 88 mg / H2SO4; CrO3 / acetone; H2O View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '113916', constants.ctx, '0')">N-bromosuccinmide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '610776', constants.ctx, '0')">triphenylphosphine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <br />T=0&deg;C;&nbsp;1&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 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 /> <br /> &nbsp;