BCl3*Me2S in dichloromethane T=20°C; 0.25 h;

1.1: 95 percent / BCl3*SMe2 / CH2Cl2 / 0.25 h / 20 °C 2.1: 96 percent / nBu3P / tetrahydrofuran / 3 h / 20 °C 3.1: silica gel / 72 h / 20 °C 3.2: 66 percent / aq. ammonium cerium nitrate / diethyl ether / 1 h / 20 °C 4.1: 80 percent / OsO4; pyridine / 24 h 5.1: 95 percent / H2O2 / tetrahydrofuran / 16 h 6.1: 4 Angstroem molecular sieves 7.1: NaH; pyridine / 1 h / 20 °C View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h / 20 &deg;C<br />2: K₂CO₃ / methanol / 1 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 99 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 &deg;C<br />2: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h / 20 &deg;C<br />3: K₂CO₃ / methanol / 1 h / 20 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4267587', constants.ctx, '0')">potassium carbonate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a> <br />T=20&deg;C;&nbsp;1&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 89 percent / NBS; PPh₃ / CH₂Cl₂ / 13 h / 20 &deg;C<br />2: 83 percent / LDA / tetrahydrofuran / 5 h / 0 &deg;C<br />3: 99 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 &deg;C<br />4: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h / 20 &deg;C<br />5: K₂CO₃ / methanol / 1 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 79 percent / NaH / tetrahydrofuran / 3 h / Heating<br />2: 89 percent / NBS; PPh₃ / CH₂Cl₂ / 13 h / 20 &deg;C<br />3: 83 percent / LDA / tetrahydrofuran / 5 h / 0 &deg;C<br />4: 99 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 &deg;C<br />5: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h / 20 &deg;C<br />6: K₂CO₃ / methanol / 1 h / 20 &deg;C<br /> <br /> &nbsp;