1.1: 90 percent / diisobutylaluminum hydride / CH2Cl2 / 0.5 h / -15 °C 2.1: NaH / diethyl ether / 0.25 h / -15 - 20 °C 2.2: diethyl ether / 2.3 h / -15 - 20 °C 3.1: 160 mg / toluene / 89 h / 140 °C 4.1: 72 percent / trifluoroacetic acid / H2O / 5 h / 0 °C 5.1: sodium periodate / methanol; H2O / 28 h / 0 - 20 °C 6.1: Jones reagent / acetone / 22 h / 0 - 5 °C 7.1: 1.34 g / NaBH4 / methanol / 3 h / 0 - 20 °C 8.1: 92 percent / 2,6-lutidine / CH2Cl2 / 43 h / 0 - 20 °C 9.1: 75 percent / sodium / liquid ammonia; tetrahydrofuran / 0.5 h / -78 °C 10.1: pyridine; trifluoroacetic acid; N,N'-dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 5 h / 20 °C 11.1: 41 mg / tetrahydrofuran / 13.75 h / -15 - 20 °C 12.1: 78 percent / pyridine; trifluoroacetic acid; N,N'-dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 7 h / 20 °C 13.1: 70 percent / triisobutylaluminum / hexane; 1,2-dichloro-ethane / 3.8 h / 0 - 20 °C 14.1: aq. trifluoroacetic acid / 17 h / 20 - 50 °C 14.2: 76 percent / sodium methoxide / methanol / 3 h / 0 °C 15.1: ozone / methanol / 0.08 h / -78 °C 15.2: dimethyl sulfide / methanol / 5 h / -78 - 20 °C 16.1: 27 mg / HOSO2NH2; NaH2PO4*2H2O; NaClO2 / 2-methyl-propan-2-ol; H2O / 0.25 h View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1.1: di-n-butyltin oxide / toluene / 3 h / Heating<br />1.2: 66 percent / cesium fluoride / dimethylformamide / 18 h / 20 &deg;C<br />2.1: CrO₃; aq. sulfuric acid / acetone / 1 h / 0 &deg;C<br />3.1: toluene / 16 h / 20 - 60 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: CrO₃; aq. sulfuric acid / acetone / 1 h / 0 &deg;C<br />2: toluene / 16 h / 20 - 60 &deg;C<br /> <br /> &nbsp;

&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=60&deg;C;&nbsp;&nbsp;Yield given;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: di-n-butyltin oxide / toluene / 3 h / Heating<br />1.2: 66 percent / cesium fluoride / dimethylformamide / 18 h / 20 &deg;C<br />2.1: CrO₃; aq. sulfuric acid / acetone / 1 h / 0 &deg;C<br />3.1: toluene / 16 h / 20 - 60 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1) Bu₂SnO, 2) CsF / 1) toluene, reflux, 2) DMF, r.t.<br />2: CrO₃, dil. H₂SO₄ / acetone / 0 &deg;C<br />3: toluene / 60 &deg;C<br /> <br /> &nbsp;