1: 83 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 2 h / 90 °C 2: (dimethylamino)pyridine / acetonitrile 3: 89 percent / tributyltin hydride, AIBN / toluene / 120 °C 4: 50 percent / LiN3, benzoic acid / dimethylformamide / 16 h / 120 °C 5: 82 percent / 0.1 M NaOCH3 / methanol View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: AcOH, conc. H₂SO₄ / CH₂Cl₂ / 16 h / 4 &deg;C<br />2: 46 percent / hexamethyldisilazane, chlorotrimethylsilane, trifluoromethanesulfonic acid / acetonitrile / 4 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 68 percent / pyridine / 16 h / -30 deg C --&gt; 25 deg C<br />2: 82 percent / DMAP / acetonitrile / 16 h / 25 &deg;C<br />3: 92 percent / Bu₃SnH, AIBN / toluene / 5 h / 120 &deg;C<br />4: 88 percent / AcOH, H₂SO₄ / CHCl₃ / 16 h / 4 &deg;C<br />5: 46 percent / HMDS, TMS-Cl, CF₃SO₃H / acetonitrile / 5 h / 80 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 82 percent / DMAP / acetonitrile / 16 h / 25 &deg;C<br />2: 92 percent / Bu₃SnH, AIBN / toluene / 5 h / 120 &deg;C<br />3: 88 percent / AcOH, H₂SO₄ / CHCl₃ / 16 h / 4 &deg;C<br />4: 46 percent / HMDS, TMS-Cl, CF₃SO₃H / acetonitrile / 5 h / 80 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 92 percent / Bu₃SnH, AIBN / toluene / 5 h / 120 &deg;C<br />2: 88 percent / AcOH, H₂SO₄ / CHCl₃ / 16 h / 4 &deg;C<br />3: 46 percent / HMDS, TMS-Cl, CF₃SO₃H / acetonitrile / 5 h / 80 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209232', constants.ctx, '0')">chloro-trimethyl-silane</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1812100', constants.ctx, '0')">trifluorormethanesulfonic acid</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '635752', constants.ctx, '0')">1,1,1,3,3,3-hexamethyl-disilazane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '741857', constants.ctx, '0')">acetonitrile</a> <br />T=80&deg;C;&nbsp;5&nbsp;h;&nbsp;<br /> &nbsp;