1: 89 percent / H2 / 5percent Pd/C / hexane / 760 Torr / Ambient temperature 2: H2O View Scheme

1: 97 percent / H2 / 5percent Pd/C / ethanol / 760 Torr 2: LiAlH4 / tetrahydrofuran 3: PBr3 / diethyl ether; diethyl ether / 16 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '385737', constants.ctx, '0')">acetic anhydride</a> <br />&nbsp;Heating;&nbsp;<br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '1343714', constants.ctx, '0')">triethyl phosponoacetate</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4122952', constants.ctx, '0')">sodium hydride</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, '8190416', constants.ctx, '0')">mineral oil</a> <br />1&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '506746', constants.ctx, '0')">1-methylcyclohexan-4-one</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, '8190416', constants.ctx, '0')">mineral oil</a> <br />T=-40&deg;C;&nbsp;3.5&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '16044005', constants.ctx, '0')">meso-tetrakis(tetraphenyl)porphyrin iron(III) chloride</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '610776', constants.ctx, '0')">triphenylphosphine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '636131', constants.ctx, '0')">benzoic acid</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=80&deg;C;&nbsp;24&nbsp;h;&nbsp;<br /> &nbsp;

&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '741857', constants.ctx, '0')">acetonitrile</a> <br />T=190&deg;C;&nbsp;0.333333&nbsp;h;&nbsp;&nbsp;microwave heating;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '508906', constants.ctx, '0')">1,8-diazabicyclo[5.4.0]undec-7-ene</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <br />T=230&deg;C;&nbsp;0.333333&nbsp;h;&nbsp;&nbsp;microwave irradiation;&nbsp;&nbsp;Title compound not separated from byproducts;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: 91 percent / Zn; iodine / benzene / 2.5 h / Heating<br />2.1: SOCl₂; pyridine / diethyl ether / 48 h / 20 &deg;C<br />2.2: 20 percent / NaOH / H₂O; ethanol / 0.33 h / 30 &deg;C<br /> <br /> &nbsp;