1: 98.5 percent / 4-dimethylaminopyridine (DMAP) / acetonitrile / Ambient temperature 2: 27 percent / α,α-azobis(isobutyronitrile) (AIBN), tributyltin hydride / toluene / 3 h / 75 - 80 °C 3: 61 percent / dichloroacetic acid / CH2Cl2 / 0.5 h / Ambient temperature 4: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran 5: 46 percent / iodine, nitric acid / dioxane / 3 h / Heating View Scheme

1: 98.5 percent / 4-dimethylaminopyridine (DMAP) / acetonitrile / Ambient temperature 2: 27 percent / α,α-azobis(isobutyronitrile) (AIBN), tributyltin hydride / toluene / 3 h / 75 - 80 °C 3: 61 percent / dichloroacetic acid / CH2Cl2 / 0.5 h / Ambient temperature 4: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran View Scheme

<b>Multi-step reaction with 6 steps<br /> </b>1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min<br />2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature<br />3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature<br />4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H₂O / 0.08 h / 0 &deg;C<br />5: 70 percent / sodium borohydride / ethanol; H₂O / 0.5 h / Ambient temperature<br />6: 81 percent / pyridine / 3.5 h / 103 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H₂O / 0.08 h / 0 &deg;C<br />2: 70 percent / sodium borohydride / ethanol; H₂O / 0.5 h / Ambient temperature<br />3: 81 percent / pyridine / 3.5 h / 103 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature<br />2: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature<br />3: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H₂O / 0.08 h / 0 &deg;C<br />4: 70 percent / sodium borohydride / ethanol; H₂O / 0.5 h / Ambient temperature<br />5: 81 percent / pyridine / 3.5 h / 103 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '103233', constants.ctx, '0')">pyridine</a> <br />T=103&deg;C;&nbsp;3.5&nbsp;h;&nbsp;<br /> &nbsp;