1.1: O3 / methanol; CH2Cl2 / -78 °C 1.2: 79 percent / NaBH4 / methanol; CH2Cl2 / -78 °C 2.1: p-TsCl; pyridine 2.2: NaN3 / aq. ethanol / 10 h / Heating 3.1: LiAlH4 / diethyl ether / Heating View Scheme

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '103233', constants.ctx, '0')">pyridine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '607898', constants.ctx, '0')">p-toluenesulfonyl chloride</a> <br /> <br />Stage #2: <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 />&nbsp;Heating;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: 41 percent / Burkholderia cepacia lipase / various solvent(s) / 24 h / 20 &deg;C / Enzymatic reaction<br />2.1: 93 percent / KOH / methanol<br />3.1: propionic acid / 140 &deg;C<br />3.2: 85 percent / NaOH / ethanol / Heating<br />4.1: 72 percent / LiAlH₄ / tetrahydrofuran<br />5.1: p-TsCl; pyridine<br />5.2: 67 percent / LiAlH₄ / tetrahydrofuran / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: 93 percent / KOH / methanol<br />2.1: propionic acid / 140 &deg;C<br />2.2: 85 percent / NaOH / ethanol / Heating<br />3.1: 72 percent / LiAlH₄ / tetrahydrofuran<br />4.1: p-TsCl; pyridine<br />4.2: 67 percent / LiAlH₄ / tetrahydrofuran / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: 72 percent / LiAlH₄ / tetrahydrofuran<br />2.1: p-TsCl; pyridine<br />2.2: 67 percent / LiAlH₄ / tetrahydrofuran / Heating<br /> <br /> &nbsp;