1: TEA / CH2Cl2 / 4 h / 0 °C 2: 1.) Mg, 2.) Li2CuCl3 / 1.) THF, 2.) 0 deg C, 3 h 3: 82 percent / PTS / methanol / Ambient temperature 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, '11378939', constants.ctx, '0')">Lindlar's catalyst</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1.) sodium hydride / 1.) THF, RT, 30 min, 2.) 2 h<br />2: LAH, ethanol / diethyl ether / 0.5 h / 0 &deg;C<br />3: H₂ / Lindlar's catalyst / hexane; ethanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: LAH, ethanol / diethyl ether / 0.5 h / 0 &deg;C<br />2: H₂ / Lindlar's catalyst / hexane; ethanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 1.) lithium amide / 1.) liquid NH₃, THF, -33 deg C, 2 h, 2.) 6 h<br />2: pyridinium chlorochromate (PCC) / CH₂Cl₂ / 1 h<br />3: 1.) sodium hydride / 1.) THF, RT, 30 min, 2.) 2 h<br />4: LAH, ethanol / diethyl ether / 0.5 h / 0 &deg;C<br />5: H₂ / Lindlar's catalyst / hexane; ethanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: pyridinium chlorochromate (PCC) / CH₂Cl₂ / 1 h<br />2: 1.) sodium hydride / 1.) THF, RT, 30 min, 2.) 2 h<br />3: LAH, ethanol / diethyl ether / 0.5 h / 0 &deg;C<br />4: H₂ / Lindlar's catalyst / hexane; ethanol<br /> <br /> &nbsp;