2: 90 percent / lithium aluminium hydride / diethyl ether / 3 h / Ambient temperature 3: 74 percent / pyridine / 24 h / Ambient temperature View Scheme

2: 90 percent / lithium aluminium hydride / diethyl ether / 3 h / Ambient temperature View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: triethylamine / CH₂Cl₂ / 1) 0 deg C, 0.5 h, 2) RT, 6 h<br />2: LiBr / acetone / 5 h / Ambient temperature<br />3: 86 percent / dimethylsulfoxide / Ambient temperature<br />4: KOH / ethane-1,2-diol / 6 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: LiBr / acetone / 5 h / Ambient temperature<br />2: 86 percent / dimethylsulfoxide / Ambient temperature<br />3: KOH / ethane-1,2-diol / 6 h / Heating<br /> <br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '3586477', constants.ctx, '0')">(4-carboxy-n-butyl)-triphenylphosphonium bromide</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3629917', constants.ctx, '0')">sodium hexamethyldisilazane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=20&deg;C;&nbsp;2&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '1236701', constants.ctx, '0')">pelargonaldehyde</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=20&deg;C;&nbsp;Wittig reaction;&nbsp;3&nbsp;h;&nbsp;&nbsp;stereoselective reaction;&nbsp;<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>2: lithium hexamethyldisilazide / tetrahydrofuran / 25 &deg;C / Reagent: DMSO-Na_. Solvent: DMSO_. <br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: toluene / 48 h / Inert atmosphere; Reflux<br />2.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / 20 &deg;C / Inert atmosphere<br />2.2: 3 h / 20 &deg;C<br /> <br /> &nbsp;