2: 99 percent / H2O2, LiOH / tetrahydrofuran; H2O / 20 h / 20 °C 3: 87 percent / PhSO2Cl, pyridine / 16 h / -20 °C 4: 100 percent / aq. HF / acetonitrile / 2 h / 20 °C 5: H2 / (Ph3P)3RhCl / benzene / 2 h / 20 °C / 760 Torr View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4123663', constants.ctx, '0')">diisobutylaluminium hydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a> <br />T=-98&deg;C;&nbsp;0.333333&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>2: 94 percent / DMAP, NEt₃ / CH₂Cl₂ / 2 h / 20 &deg;C<br />3: 1) Me₃SiCl, NEt₃, LDA, 2) aq. HCl / 1) THF, -78 deg C, 1 h, then 20 deg C, 1 h, then 60 deg C, 2 h<br />4: diethyl ether / 0 &deg;C<br />5: 80 percent / DIBAL / diethyl ether / 0.33 h / -98 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 &deg;C<br />4: 94 percent / DMAP, NEt₃ / CH₂Cl₂ / 2 h / 20 &deg;C<br />5: 1) Me₃SiCl, NEt₃, LDA, 2) aq. HCl / 1) THF, -78 deg C, 1 h, then 20 deg C, 1 h, then 60 deg C, 2 h<br />6: diethyl ether / 0 &deg;C<br />7: 80 percent / DIBAL / diethyl ether / 0.33 h / -98 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 &deg;C<br />4: 94 percent / DMAP, NEt₃ / CH₂Cl₂ / 2 h / 20 &deg;C<br />5: 1) Me₃SiCl, NEt₃, LDA, 2) aq. HCl / 1) THF, -78 deg C, 1 h, then 20 deg C, 1 h, then 60 deg C, 2 h<br />6: diethyl ether / 0 &deg;C<br />7: 80 percent / DIBAL / diethyl ether / 0.33 h / -98 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 &deg;C<br />3: 94 percent / DMAP, NEt₃ / CH₂Cl₂ / 2 h / 20 &deg;C<br />4: 1) Me₃SiCl, NEt₃, LDA, 2) aq. HCl / 1) THF, -78 deg C, 1 h, then 20 deg C, 1 h, then 60 deg C, 2 h<br />5: diethyl ether / 0 &deg;C<br />6: 80 percent / DIBAL / diethyl ether / 0.33 h / -98 &deg;C<br /> <br /> &nbsp;