1.1: 71 percent / Et3N / CH2Cl2 / 1 h / 0 °C 2.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 3.1: 81 percent / pyridine / 3 h / Heating 4.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 5.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 6.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 7.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 8.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 9.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 10.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 10.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 11.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 12.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '605283', constants.ctx, '0')">triethylamine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '11378939', constants.ctx, '0')">Lindlar's catalyst</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br />T=-10 - -4&deg;C;&nbsp;Catalytic hydrogenation;&nbsp;16&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: AD-mix-β; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 16 h / 0 &deg;C<br />2: KOH / H₂O; methanol / 60 &deg;C<br />3: 2.12 g / TsOH / CH₂Cl₂ / 0.5 h / 20 &deg;C<br />4: 68 percent / Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 8 h / 20 &deg;C<br />5: 92 percent / H₂; Et₃N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 68 percent / Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 8 h / 20 &deg;C<br />2: 92 percent / H₂; Et₃N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1.1: 9-BBN / tetrahydrofuran / 16 h / 0 - 20 &deg;C<br />1.2: 42 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 1.5 h / 20 &deg;C<br />2.1: 90 percent / PCC; celite / CH₂Cl₂ / 2 h / 20 &deg;C<br />3.1: KN(SiMe₃)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 &deg;C<br />3.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 &deg;C<br />4.1: AD-mix-β; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 16 h / 0 &deg;C<br />5.1: KOH / H₂O; methanol / 60 &deg;C<br />6.1: 2.12 g / TsOH / CH₂Cl₂ / 0.5 h / 20 &deg;C<br />7.1: 68 percent / Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 8 h / 20 &deg;C<br />8.1: 92 percent / H₂; Et₃N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 10 steps<br /> </b>1.1: nBuLi / tetrahydrofuran / 2 h / -78 - 0 &deg;C<br />2.1: 9.95 g / p-TsOH / methanol; H₂O / 1 h / 20 &deg;C<br />3.1: 91 percent / I₂; imidazole; PPh₃ / toluene / 2 h / 20 &deg;C<br />4.1: 99 percent / acetonitrile / 16 h / Heating<br />5.1: KN(SiMe₃)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 &deg;C<br />5.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 &deg;C<br />6.1: AD-mix-β; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 16 h / 0 &deg;C<br />7.1: KOH / H₂O; methanol / 60 &deg;C<br />8.1: 2.12 g / TsOH / CH₂Cl₂ / 0.5 h / 20 &deg;C<br />9.1: 68 percent / Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 8 h / 20 &deg;C<br />10.1: 92 percent / H₂; Et₃N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 11 steps<br /> </b>1.1: 96 percent / p-TsOH / diethyl ether / 2 h / 20 &deg;C<br />2.1: nBuLi / tetrahydrofuran / 2 h / -78 - 0 &deg;C<br />3.1: 9.95 g / p-TsOH / methanol; H₂O / 1 h / 20 &deg;C<br />4.1: 91 percent / I₂; imidazole; PPh₃ / toluene / 2 h / 20 &deg;C<br />5.1: 99 percent / acetonitrile / 16 h / Heating<br />6.1: KN(SiMe₃)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 &deg;C<br />6.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 &deg;C<br />7.1: AD-mix-β; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 16 h / 0 &deg;C<br />8.1: KOH / H₂O; methanol / 60 &deg;C<br />9.1: 2.12 g / TsOH / CH₂Cl₂ / 0.5 h / 20 &deg;C<br />10.1: 68 percent / Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 8 h / 20 &deg;C<br />11.1: 92 percent / H₂; Et₃N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 &deg;C<br /> <br /> &nbsp;