1: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature 2: 82 percent / NaHCO3 / aq. ethanol 3: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature 4: 79 percent / aq. NaIO4 / methanol / 2 h 5: 88 percent / NaBH4 / methanol / 0.5 h View Scheme

1: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature 2: 82 percent / NaHCO3 / aq. ethanol 3: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature 4: 79 percent / aq. NaIO4 / methanol / 2 h 5: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h View Scheme

1: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature 2: 82 percent / NaHCO3 / aq. ethanol 3: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature 4: 79 percent / aq. NaIO4 / methanol / 2 h 5: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h 6: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 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, '1730733', constants.ctx, '0')">hexane</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '8400700', constants.ctx, '0')">Petroleum ether</a> <br />T=-78&deg;C;&nbsp;1&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 91 percent / NaN₃ / dimethylformamide / 12 h / 100 &deg;C<br />2: 82 percent / DIBAL / light petroleum; toluene; hexane / 1 h / -78 &deg;C<br /> <br /> &nbsp;