2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in toluene 5 h; Heating;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1.) TMEDA, n-BuLi / 1) THF, 0 deg C, 20 min; 2) THF, rt, 3 h<br />2: 70 percent / conc. HCl / methanol / 2 h / Heating<br />3: 1.) NaH / 1) acetonitrile, reflux, 1 h; 2) acetonitrile, reflux, 2 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 70 percent / conc. HCl / methanol / 2 h / Heating<br />2: 1.) NaH / 1) acetonitrile, reflux, 1 h; 2) acetonitrile, reflux, 2 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 67 percent / Et₃N / CH₂Cl₂ / Ambient temperature<br />2: 1.) TMEDA, n-BuLi / 1) THF, 0 deg C, 20 min; 2) THF, rt, 3 h<br />3: 70 percent / conc. HCl / methanol / 2 h / Heating<br />4: 1.) NaH / 1) acetonitrile, reflux, 1 h; 2) acetonitrile, reflux, 2 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1.) sodium borohydride / 1) ethanol, 0 deg C, 30 min; 2) ethanol, rt, 16 h<br />2: 77 percent / sodium iodide / acetone / 18 h / Heating<br />3: 1.) NaH / 1) acetonitrile, reflux, 1 h; 2) acetonitrile, reflux, 2 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1.) TMEDA, n-BuLi / 1) THF, 0 deg C, 20 min; 2) THF, rt, 3 h<br />2: 70 percent / conc. HCl / methanol / 2 h / Heating<br />3: 1.) NaH / 1) acetonitrile, reflux, 1 h; 2) acetonitrile, reflux, 2 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 68 percent / n-BuLi / tetrahydrofuran / -78 &deg;C<br />2: 70 percent / H⁽¹⁺⁾ / methanol / Heating<br />3: 44 percent / NaH / tetrahydrofuran<br /> <br /> &nbsp;