1195-59-1

39621-11-9

GENERAL STEPS: The reaction was carried out in the presence of a base using complex 1 as a catalyst. This was done as follows: in a round-bottomed flask, 1 mmol of 2,6-pyridinedimethanol, 0.005 mmol of catalyst (3.6 mg) and 0.010 mmol of tBuOK (1.1 mg) were dissolved in 10 mL of toluene. The reaction mixture was placed in an aerobic environment and stirred continuously at 50 °C for 6 hours. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure using a rotary evaporator. The resulting crude product was purified by preparative silica gel GF-254 thin layer chromatography (TLC) with the eluent being a solvent mixture of ethyl acetate: hexane (1:10). The structure of the final product, 6-(hydroxymethyl)pyridinecarboxaldehyde, was confirmed by NMR spectroscopy (for the relevant spectra, see Figures S4-S32).