triethylamine in dichloromethane T=0°C; 0.666667 h;

pyridine T=20°C; 15 h;

With  pyridinium chlorochromate in  dichloromethane 2 h;  Ambient temperature;   

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '11378932', constants.ctx, '0')">Pd-BaSO₄</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a> <br /> <br /> &nbsp;

<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, '1696894', constants.ctx, '0')">diethyl ether</a> <br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: p-TSA / methanol<br />2: H₂ / Pd/BaSO₄ <br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 1.) tetrapropyldiborane, 2.) aq. NaOH, aq. H₂O₂ / 1) THF, 0 deg C, 30 min, 0 --&gt; 20 deg C, 2 h; 2) THF, MeOH, - 5 deg C; further reagents: dimethyl sulfate, NaBH₄ <br />2: 55 percent / pyridinium chlorochromate, CH₃COONa / CH₂Cl₂ <br />3: 1.) (Me₃Si)2NNa / 1) THF, room temperature, 30 min, reflux, 1 h; 2) -78 --&gt; 20 deg C, overnight (room temperature)<br />4: 94 percent / LiAlH₄ / diethyl ether<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: p-TSA<br />2: n-BuLi<br />3: p-TSA / methanol<br />4: H₂ / Pd/BaSO₄ <br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: n-BuLi<br />2: p-TSA / methanol<br />3: H₂ / Pd/BaSO₄ <br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1.) n-BuLi / 1) THF; 2) HMPT, THF, below 25 deg C, 0.5 h<br />2: 100 percent / PPTS / ethanol / 3 h / 70 &deg;C<br />3: 96 percent / H₂ / Pd/BaSO₄ / methanol<br /> <br /> &nbsp;