1: pyridinium p-toluenesulfonate / 1 h / 20 °C 2: 4.4 g / BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 3: methanol; pyridinium p-toluenesulfonate / 18 h / Heating 4: 1.92 g / triethylamine / CH2Cl2 / 1 h / 20 °C 5: hydrochloric acid / 42 h / 60 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4151240', constants.ctx, '0')">lithium triethylborohydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1.1: 98 percent / sodium hydride / tetrahydrofuran / 16 h / 0 - 20 &deg;C<br />2.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 &deg;C<br />3.1: hydrogen / 20percent Pd(OH)2 on carbon / CH₂Cl₂ / 3.5 h<br />4.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH₂Cl₂ / 1.5 h / 20 &deg;C<br />5.1: pyridinium p-toluenesulfonate; MgSO₄ / diethyl ether / 18 h / 20 &deg;C<br />6.1: 52 percent / BF₃*Et₂O / diethyl ether / 3 h / -78 - -50 &deg;C<br />7.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating<br />7.2: CuBr*Me₂S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 &deg;C<br />7.3: 6.9 g / tetrahydrofuran / 1 h / -78 &deg;C<br />8.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 9 steps<br /> </b>1.1: 63 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 &deg;C<br />2.1: 98 percent / sodium hydride / tetrahydrofuran / 16 h / 0 - 20 &deg;C<br />3.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 &deg;C<br />4.1: hydrogen / 20percent Pd(OH)2 on carbon / CH₂Cl₂ / 3.5 h<br />5.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH₂Cl₂ / 1.5 h / 20 &deg;C<br />6.1: pyridinium p-toluenesulfonate; MgSO₄ / diethyl ether / 18 h / 20 &deg;C<br />7.1: 52 percent / BF₃*Et₂O / diethyl ether / 3 h / -78 - -50 &deg;C<br />8.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating<br />8.2: CuBr*Me₂S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 &deg;C<br />8.3: 6.9 g / tetrahydrofuran / 1 h / -78 &deg;C<br />9.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 &deg;C<br />2.1: hydrogen / 20percent Pd(OH)2 on carbon / CH₂Cl₂ / 3.5 h<br />3.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH₂Cl₂ / 1.5 h / 20 &deg;C<br />4.1: pyridinium p-toluenesulfonate; MgSO₄ / diethyl ether / 18 h / 20 &deg;C<br />5.1: 52 percent / BF₃*Et₂O / diethyl ether / 3 h / -78 - -50 &deg;C<br />6.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating<br />6.2: CuBr*Me₂S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 &deg;C<br />6.3: 6.9 g / tetrahydrofuran / 1 h / -78 &deg;C<br />7.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: hydrogen / 20percent Pd(OH)2 on carbon / CH₂Cl₂ / 3.5 h<br />2.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH₂Cl₂ / 1.5 h / 20 &deg;C<br />3.1: pyridinium p-toluenesulfonate; MgSO₄ / diethyl ether / 18 h / 20 &deg;C<br />4.1: 52 percent / BF₃*Et₂O / diethyl ether / 3 h / -78 - -50 &deg;C<br />5.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating<br />5.2: CuBr*Me₂S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 &deg;C<br />5.3: 6.9 g / tetrahydrofuran / 1 h / -78 &deg;C<br />6.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: CuBr*SMe₂; trimethylsilylchloride / tetrahydrofuran / 0.5 h / -30 - -20 &deg;C<br />1.2: 97.6 percent / tetrahydrofuran; toluene / 0.42 h / -20 &deg;C<br />2.1: LiEt₃BH / tetrahydrofuran<br /> <br /> &nbsp;