1.1: tetrahydrofuran / 80 °C 1.2: 0.473 g / PhLi / tetrahydrofuran / 0.67 h 2.1: p-toluenesulfonic acid monohydrate / methanol / 4 h / 50 °C 3.1: aq. NaIO4 / CH2Cl2 / 0.75 h 4.1: 0.269 g / NaBH4 / methanol / 1 h / 0 °C 5.1: 92 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4123663', constants.ctx, '0')">diisobutylaluminium hydride</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=-78&deg;C;&nbsp;2&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 92 percent / H₂ / Pd(OH)2-C / methanol / 12 h / 103430 Torr<br />2: DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 &deg;C<br /> <br /> &nbsp;