1: 78 percent / Br2, azobisisobutylonitrile / CCl4 / 2 h / 70 °C 2: 57 percent / 1 N aq. KOH / 2 h / 0 °C View Scheme

1: 78 percent / Br2, azobisisobutylonitrile / CCl4 / 2 h / 70 °C 2: 99 percent / AgNO3 / acetone; H2O / 2 h / Ambient temperature View Scheme

<b>Multi-step reaction with 9 steps<br /> </b>1: 83 percent / 1.) TMSCl, NaBr, 2.) DMSO / acetonitrile / 2 h / Ambient temperature<br />2: 88 percent / pyridine, DMAP / CH₂Cl₂ / 4 h / Ambient temperature<br />3: 1.) aq. Na₂S₂O₄, 2.) pyridine, DMAP / 1.) ether, 2.) CH₂Cl_2. RT<br />4: 100 percent / CF₃COOH / CH₂Cl₂ / 12 h / 0 &deg;C<br />5: 69 percent / BH₃ / tetrahydrofuran / 6 h / 0 &deg;C<br />6: 64 percent / pyridinium chlorochromate, Celite / CH₂Cl₂ / 3 h / Ambient temperature<br />7: 46 percent / diethyl ether; tetrahydrofuran / 2 h / -78 &deg;C<br />8: 85 percent / pyridinium chlorochromate, Celite / CH₂Cl₂ / 3 h / Ambient temperature<br />9: 34 percent / ethanol; tetrahydrofuran / 2 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 1.) aq. Na₂S₂O₄, 2.) pyridine, DMAP / 1.) ether, 2.) CH₂Cl_2. RT<br />2: 100 percent / CF₃COOH / CH₂Cl₂ / 12 h / 0 &deg;C<br />3: 69 percent / BH₃ / tetrahydrofuran / 6 h / 0 &deg;C<br />4: 64 percent / pyridinium chlorochromate, Celite / CH₂Cl₂ / 3 h / Ambient temperature<br />5: 46 percent / diethyl ether; tetrahydrofuran / 2 h / -78 &deg;C<br />6: 85 percent / pyridinium chlorochromate, Celite / CH₂Cl₂ / 3 h / Ambient temperature<br />7: 34 percent / ethanol; tetrahydrofuran / 2 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 46 percent / diethyl ether; tetrahydrofuran / 2 h / -78 &deg;C<br />2: 85 percent / pyridinium chlorochromate, Celite / CH₂Cl₂ / 3 h / Ambient temperature<br />3: 34 percent / ethanol; tetrahydrofuran / 2 h / -78 &deg;C<br /> <br /> &nbsp;

&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br />T=-78&deg;C;&nbsp;2&nbsp;h;&nbsp;<br /> &nbsp;