N,O-bis-(trimethylsilyl)-acetamide; 1,4-di(diphenylphosphino)-butane; tris-(dibenzylideneacetone)dipalladium(0) in toluene T=110°C; 1 h;

1: 69 percent / decarbethoxylation (A. P. Krapcho, A. J. Lovey, Tetrahedron Lett., 957 (1973)) 2: hydrolysis View Scheme

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '774687', constants.ctx, '0')">diethyl malonate</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 />T=0&deg;C;&nbsp;0.5&nbsp;h;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '3117674', constants.ctx, '0')">(4-bromobut-1-yn-1-yl)benzene</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=20&deg;C;&nbsp;1&nbsp;h;&nbsp;<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11405916', constants.ctx, '0')">copper(l) iodide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '11604118', constants.ctx, '0')">tetrakis(triphenylphosphine) palladium⁽⁰⁾</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '605283', constants.ctx, '0')">triethylamine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=50&deg;C;&nbsp;17&nbsp;h;&nbsp;&nbsp;Inert atmosphereSchlenk technique;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 25 &deg;C / |Inert atmosphere; |Schlenk technique<br />1.2: 15 h / 65 &deg;C / |Inert atmosphere; |Schlenk technique<br />2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; triethylamine / tetrahydrofuran / 17 h / 50 &deg;C / |Inert atmosphere; |Schlenk technique<br /> <br /> &nbsp;