1: 1.) n-BuLi / 1.) THF, hexane, -75 deg C, 1 h; 2.) THF, hexane, r.t., 72 h 2: 1.) Na-K eutectic alloy / 1.) Et2O, reflux, 1 h; 2.) Et2O, -10 deg C then r.t., overnight 3: 1.) Cs-K-Na alloy; 2.) CO2; 3.) CH2N2 / 1.) THF, -75 deg C, 2 min; 2.) THF, -75 deg C View Scheme

phosphorus; hydrogen iodide

(i) nBuLi, Et2O, pentane, (ii) DMSO, (iii) /BRN= 385801/; Multistep reaction;

&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=-78 - 0&deg;C;&nbsp;4&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br /> &nbsp;

&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '969132', constants.ctx, '0')">pentane</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '969212', constants.ctx, '0')">benzene</a> <br />T=0&deg;C;&nbsp;4&nbsp;h;&nbsp;<br /> &nbsp;

&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />2&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;&nbsp;Yield given;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '969212', constants.ctx, '0')">benzene</a> <br /> <br /> &nbsp;