1: thionyl chloride / CH2Cl2 / 0.08 h / 20 °C 2: 1,8-DBU / benzene / Heating 3: 73 percent / AD-mix-β; CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 24 h / 0 °C 4: 3M HCl / H2O; methanol / 5 h / 60 °C View Scheme

1: thionyl chloride / CH2Cl2 / 0.08 h / 20 °C 2: 1,8-DBU / benzene / Heating 3: 73 percent / AD-mix-β; CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 24 h / 0 °C 4: 3M HCl / H2O; methanol / 5 h / 60 °C View Scheme

1: thionyl chloride / CH2Cl2 / 0.08 h / 20 °C 2: 1,8-DBU / benzene / Heating 3: 75 percent / AD-mix-α; CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 24 h / 0 °C 4: 3M HCl / H2O; methanol / 5 h / 60 °C View Scheme

Stage #1: <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, '11378922', constants.ctx, '0')">palladium on activated charcoal</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br />T=20&deg;C;&nbsp;Reduction;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11343078', constants.ctx, '0')">sodium tetrahydroborate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br />Reduction;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: 50 percent aq. KOH / ethanol / 0.5 h / 20 &deg;C<br />1.2: 55 percent / ethanol<br />2.1: H₂ / 5 percent Pd/C / ethanol / 20 &deg;C<br />2.2: 99 percent / NaBH₄ / ethanol<br /> <br /> &nbsp;