hydrogenchloride in ethanol 1 h; Heating; Yield given;

1: conc. HCl / ethanol / 1 h / Heating 2: 1.) OsO4, 2.) H2S / 1.) THF, RT, 18 h View Scheme

<b>Multi-step reaction with 7 steps<br /> </b>1: ethanol; H₂O / 12 h / Heating<br />2: 76 percent / aq. KOH / ethanol / 3 h / Heating<br />3: 83 percent / polyphosphoric acid / toluene / 4 h / Heating<br />4: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH₂Cl₂ / 0.5 h<br />5: 58 percent / pyridine hydrochloride / 0.5 h / 210 &deg;C<br />6: 90 percent / K₂CO₃ / acetone / 3 h / Heating<br />7: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: thionyl chloride / toluene / 1 h / 80 &deg;C<br />2: ethanol; H₂O / 12 h / Heating<br />3: 76 percent / aq. KOH / ethanol / 3 h / Heating<br />4: 83 percent / polyphosphoric acid / toluene / 4 h / Heating<br />5: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH₂Cl₂ / 0.5 h<br />6: 58 percent / pyridine hydrochloride / 0.5 h / 210 &deg;C<br />7: 90 percent / K₂CO₃ / acetone / 3 h / Heating<br />8: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 76 percent / aq. KOH / ethanol / 3 h / Heating<br />2: 83 percent / polyphosphoric acid / toluene / 4 h / Heating<br />3: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH₂Cl₂ / 0.5 h<br />4: 58 percent / pyridine hydrochloride / 0.5 h / 210 &deg;C<br />5: 90 percent / K₂CO₃ / acetone / 3 h / Heating<br />6: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH₂Cl₂ / 0.5 h<br />2: 58 percent / pyridine hydrochloride / 0.5 h / 210 &deg;C<br />3: 90 percent / K₂CO₃ / acetone / 3 h / Heating<br />4: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 90 percent / K₂CO₃ / acetone / 3 h / Heating<br />2: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 83 percent / polyphosphoric acid / toluene / 4 h / Heating<br />2: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH₂Cl₂ / 0.5 h<br />3: 58 percent / pyridine hydrochloride / 0.5 h / 210 &deg;C<br />4: 90 percent / K₂CO₃ / acetone / 3 h / Heating<br />5: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 58 percent / pyridine hydrochloride / 0.5 h / 210 &deg;C<br />2: 90 percent / K₂CO₃ / acetone / 3 h / Heating<br />3: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h<br /> <br /> &nbsp;