1: 82 percent / diphenylphosphoryl azide (DPPA), triethylamine / 0.5 h / 80 °C 2: 81 percent / AcOH / H2O / 1 h / 80 °C View Scheme

sodium hydroxide; diphenylphosphoranyl azide; acetic acid; triethylamine Multistep reaction;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11342940', constants.ctx, '0')">sodium hydroxide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br />5&nbsp;h;&nbsp;&nbsp;Heating;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 20percent aqueous NaOH / ethanol / 12 h / Heating<br />2: 77 percent / diethyl ether; methanol; CHCl₃ / 0.17 h / 0 &deg;C<br />3: 94 percent / AcOH, polyphosphoric acid / acetonitrile / 12 h / Ambient temperature<br />4: 87 percent / NH₂OH*HCl, NaOAc / ethanol / 1 h / Heating<br />5: 55 percent / xylene / 24 h / Heating<br />6: 90 percent / 10percent aqueous NaOH / ethanol / 1 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 1.5 h / 180 &deg;C<br />2: 20percent aqueous NaOH / ethanol / 12 h / Heating<br />3: 77 percent / diethyl ether; methanol; CHCl₃ / 0.17 h / 0 &deg;C<br />4: 94 percent / AcOH, polyphosphoric acid / acetonitrile / 12 h / Ambient temperature<br />5: 87 percent / NH₂OH*HCl, NaOAc / ethanol / 1 h / Heating<br />6: 55 percent / xylene / 24 h / Heating<br />7: 90 percent / 10percent aqueous NaOH / ethanol / 1 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 77 percent / diethyl ether; methanol; CHCl₃ / 0.17 h / 0 &deg;C<br />2: 94 percent / AcOH, polyphosphoric acid / acetonitrile / 12 h / Ambient temperature<br />3: 87 percent / NH₂OH*HCl, NaOAc / ethanol / 1 h / Heating<br />4: 55 percent / xylene / 24 h / Heating<br />5: 90 percent / 10percent aqueous NaOH / ethanol / 1 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 94 percent / AcOH, polyphosphoric acid / acetonitrile / 12 h / Ambient temperature<br />2: 87 percent / NH₂OH*HCl, NaOAc / ethanol / 1 h / Heating<br />3: 55 percent / xylene / 24 h / Heating<br />4: 90 percent / 10percent aqueous NaOH / ethanol / 1 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 87 percent / NH₂OH*HCl, NaOAc / ethanol / 1 h / Heating<br />2: 55 percent / xylene / 24 h / Heating<br />3: 90 percent / 10percent aqueous NaOH / ethanol / 1 h / Heating<br /> <br /> &nbsp;