1.1: 100 percent / NaBH4 / methanol / 0.75 h / 0 - 20 °C 2.1: 77 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 95 percent / Mo7O24(NH4)6*4H2O; H2O2 / ethanol; H2O / 18 h / 20 °C 4.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 4.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 5.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 6.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 7.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 7.2: CH2Cl2 / 3 h / -78 - 20 °C 8.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 9.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 10.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C 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, '1730800', constants.ctx, '0')">dichloromethane</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=-78&deg;C;&nbsp;4&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 95 percent / dimethylsulfoxide / 5 h / 85 &deg;C<br />2: 84 percent / DIBAL-H / CH₂Cl₂; toluene / 4 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 10 steps<br /> </b>1.1: 95 percent / H₂SO₄ / benzene / 18 h / Heating<br />2.1: α-chymotrypsin; NaOH / aq. phosphate buffer / 90 h / 20 &deg;C / pH 7.5 - 7.8<br />3.1: 99 percent / B(OMe)3; BH₃*DMS / tetrahydrofuran / 42 h / 20 &deg;C<br />4.1: 86 percent / imidasole / dimethylformamide / 18 h / 20 &deg;C<br />5.1: 96 percent / DIBAL-H / toluene; heptane / 2 h / -78 &deg;C<br />6.1: sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 &deg;C<br />6.2: 91 percent / Bu₄NI / dimethylformamide; various solvent(s) / 18 h / 20 &deg;C<br />7.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 &deg;C<br />8.1: 98 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 18 h / 20 &deg;C<br />9.1: 95 percent / dimethylsulfoxide / 5 h / 85 &deg;C<br />10.1: 84 percent / DIBAL-H / CH₂Cl₂; toluene / 4 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1.1: 99 percent / B(OMe)3; BH₃*DMS / tetrahydrofuran / 42 h / 20 &deg;C<br />2.1: 86 percent / imidasole / dimethylformamide / 18 h / 20 &deg;C<br />3.1: 96 percent / DIBAL-H / toluene; heptane / 2 h / -78 &deg;C<br />4.1: sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 &deg;C<br />4.2: 91 percent / Bu₄NI / dimethylformamide; various solvent(s) / 18 h / 20 &deg;C<br />5.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 &deg;C<br />6.1: 98 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 18 h / 20 &deg;C<br />7.1: 95 percent / dimethylsulfoxide / 5 h / 85 &deg;C<br />8.1: 84 percent / DIBAL-H / CH₂Cl₂; toluene / 4 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: 96 percent / DIBAL-H / toluene; heptane / 2 h / -78 &deg;C<br />2.1: sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 &deg;C<br />2.2: 91 percent / Bu₄NI / dimethylformamide; various solvent(s) / 18 h / 20 &deg;C<br />3.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 &deg;C<br />4.1: 98 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 18 h / 20 &deg;C<br />5.1: 95 percent / dimethylsulfoxide / 5 h / 85 &deg;C<br />6.1: 84 percent / DIBAL-H / CH₂Cl₂; toluene / 4 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1.1: 86 percent / imidasole / dimethylformamide / 18 h / 20 &deg;C<br />2.1: 96 percent / DIBAL-H / toluene; heptane / 2 h / -78 &deg;C<br />3.1: sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 &deg;C<br />3.2: 91 percent / Bu₄NI / dimethylformamide; various solvent(s) / 18 h / 20 &deg;C<br />4.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 &deg;C<br />5.1: 98 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 18 h / 20 &deg;C<br />6.1: 95 percent / dimethylsulfoxide / 5 h / 85 &deg;C<br />7.1: 84 percent / DIBAL-H / CH₂Cl₂; toluene / 4 h / -78 &deg;C<br /> <br /> &nbsp;