1: 75 percent / SnCl2*H2O / methanol / 0.67 h / Heating 2: 68 percent / HgCl2, CaCO3 / acetonitrile; H2O / 24 h / Ambient temperature 3: 89 percent / 1,4-cyclohexadiene / Pd-C / ethanol / 3 h / 20 °C View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: DIBAL-H / CH₂Cl₂ / -78 &deg;C<br />2: TMSCl<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: NaOH<br />2: HNO₃; H₂SO₄ / CH₂Cl₂ / -25 &deg;C<br />3: SOCl₂ / benzene<br />4: TFA / tetrahydrofuran<br />5: H₂SO₄ / Heating<br />6: DIBAL-H / CH₂Cl₂ / -78 &deg;C<br />7: TMSCl<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: NaOH<br />2: HNO₃; H₂SO₄ / CH₂Cl₂ / -25 &deg;C<br />3: SOCl₂ / benzene<br />4: TFA / tetrahydrofuran<br />5: H₂SO₄ / Heating<br />6: DIBAL-H / CH₂Cl₂ / -78 &deg;C<br />7: TMSCl<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 76 percent / NaOH / tetrahydrofuran; H₂O / 48 h / Heating<br />2: 83 percent / SnCl₄, HNO₃ / CH₂Cl₂ / 0.08 h / -25 &deg;C<br />3: 1.) oxalyl chloride, DMF 2.) Et₃N / 1. THF, r. t., 3h 2. THF, H₂O, r. t., 1.5h<br /> <br /> &nbsp;