1: toluene / 18 h / Molecular sieve; Reflux 2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 18 h / 0 - 20 °C 3: pyridine hydrogenfluoride / tetrahydrofuran / 7 h / 0 - 20 °C View Scheme

1: 1.99 g / diethyl ether / 1 h / -78 °C 2: 83 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 2 h / -78 - -20 °C 3: 51 percent / HCl; NaBH3CN / methanol / 24 h / 20 °C 4: 83 percent / H2SO4 / methanol / 3.5 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, '1730800', constants.ctx, '0')">dichloromethane</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=-78&deg;C;&nbsp;12&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: I₂ / methanol / 4 h<br />2: 67 percent / (COCl)2; DMSO / CH₂Cl₂ / -50 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: imidazole / dimethylformamide / 18 h<br />2: I₂ / methanol / 4 h<br />3: 67 percent / (COCl)2; DMSO / CH₂Cl₂ / -50 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 95 percent / imidazole / dimethylformamide / 0.5 h / 0 &deg;C<br />2: 99 percent / LiAlH₄ / diethyl ether / 1.75 h / 20 &deg;C<br />3: 3.59 g / pyridinium chlorochromate / CH₂Cl₂ / 5 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 2,6-dimethylpyridine / dichloromethane / 3 h / -78 &deg;C / |Inert atmosphere<br />2: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 &deg;C / |Inert atmosphere<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 95 percent / imidazole / dimethylformamide / 0.5 h / 0 &deg;C<br />2: 99 percent / LiAlH₄ / diethyl ether / 1.75 h / 20 &deg;C<br />3: 3.59 g / pyridinium chlorochromate / CH₂Cl₂ / 5 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: potassium <i>tert</i>-butylate / tetrahydrofuran / 4.5 h / 0 - 20 &deg;C / |Cooling with ice<br />2: trifluoroacetic acid / water; dichloromethane / 18 h / 20 &deg;C<br /> <br /> &nbsp;