1: diisobutylaluminum hydride / CH2Cl2 / 1 h / -78 °C 2: pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature 3: 1) LDA, 2) (CO2H)2 / 1) THF, -78 deg C to 20 deg C, 2) 1.5h, r.t. 4: 1) CrCl3, LiAlH4, 2) DIBAL / 1) THF, 0 deg C, 10 min to r.t., 45 min, 2) CH2Cl2, -50 deg C, 30 min 5: 33 percent / 1) CuSO4/SiO2, 2) 46percent HF / 1) C6H6, 50 deg C, 1.5h, 2) MeOH, THF, r.t., 5h View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: 84 percent / pyridine / 96 h / Ambient temperature<br />2: 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '105690', constants.ctx, '0')">2,6-dimethylpyridine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />0.5&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;&nbsp;Yield given;&nbsp;<br /> &nbsp;