1: triphenylphosphine / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere 2: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 3: diisopropylamine; copper(I) bromide / 1,4-dioxane / 7 h / Inert atmosphere; Reflux 4: toluene / 3 h / Inert atmosphrere; Reflux View Scheme

1: 55 percent / Hg(OAc)2, H2SO4 / acetic acid; H2O / 3 h / Ambient temperature 2: 88 percent / aq. KOH / tetrahydrofuran; methanol / 2 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11460447', constants.ctx, '0')">lithium aluminium tetrahydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=40 - 45&deg;C;&nbsp;2&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 85 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / 6 h / Ambient temperature<br />2: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / 40 - 45 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 &deg;C<br />1.2: 20 &deg;C<br />2.1: diisobutylaluminium hydride / toluene; hexane / -78 - 20 &deg;C / |Inert atmosphere<br /> <br /> &nbsp;