1: KH (22percent) / benzene / Ambient temperature 2: 92 percent / p-toluenesulfonic acid monohydrate / methanol / Heating 3: 1.) NEt3; 2.) KCl (0.1N) / 1.) CHCl3, room temp., 6h; 40 deg C, 12 h; 2.) 1 h 4: 2.) AgOAc / 1.) methanol, 55 deg C, overnight; 2.) 90 percent aqueous methanol, 2 h 5: 95 percent / H2 / palladium black / ethanol / 72 h / 50 °C / 760 Torr 6: 93 percent / pyridine / 2 h / 70 °C View Scheme

1: KH (22percent) / benzene / Ambient temperature 2: 92 percent / p-toluenesulfonic acid monohydrate / methanol / Heating 3: 1.) NEt3; 2.) KCl (0.1N) / 1.) CHCl3, room temp., 6h; 40 deg C, 12 h; 2.) 1 h 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, '11378922', constants.ctx, '0')">palladium on activated charcoal</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br />P=3040&nbsp;Torr;&nbsp;48&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 87 percent / PPh₃/H₃COCON=NCOOCH₃ / tetrahydrofuran / Ambient temperature<br />2: 94 percent / H₂ / Pd-C / ethanol; tetrahydrofuran / 48 h / 3040 Torr / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: sodium hydride / toluene / 6 h / |Reflux<br />2: hydrochlorid acid / methanol / 3 h / |Reflux<br />3: triethylamine / toluene / 5 h / |Reflux<br /> <br /> &nbsp;