1: 57 percent / 4A molecular sieves, N-methylmorpholine N-oxide, tetra-n-propylammonium perruthenate / tetrahydrofuran / 14 h / Ambient temperature 2: 1.) azobis(isobutyronitrile), tri-n-butyltin hydride, 2.) iodine / 1.) benzene, reflux, 3 h, 2.) CH2Cl2 View Scheme

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '906752', constants.ctx, '0')">trimethylsilylacetylene</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209227', constants.ctx, '0')">n-butyllithium</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, '1730733', constants.ctx, '0')">hexane</a> <br />T=-40 - -20&deg;C;&nbsp;1&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '1884007', constants.ctx, '0')">Epiandrosterone</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, '1730733', constants.ctx, '0')">hexane</a> <br />T=-40&deg;C;&nbsp;1&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;&nbsp;Further stages;&nbsp;<br /> &nbsp;

&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />20&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 1.) CH₃Li / 1.) ether, from 0 deg C to RT, 1 h, 2.) THF, from 0 deg C to RT, 4 h<br />2: aq. KOH / methanol / 0.5 h / 65 - 70 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3556712', constants.ctx, '0')">potassium <i>tert</i>-butylate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '906698', constants.ctx, '0')"><i>tert</i>-butyl alcohol</a> <br /> <br /> &nbsp;