Dimethyl Sulfoxide → 4-(4-Pyridyl)benzaldehyde

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Reaction Steps

To a cooled (−78° C.) solution of oxalyl chloride in CH2Cl2 (15 mL, 1M) is added, dropwise, DMSO (3 mL). The resulting solution is stirred for 5 minutes then a solution of 4-[pyridin-4-yl]-benzyl alcohol (2.80 g, 15 mmol) (reference example 13a) in CH2Cl2/DMSO (27 mL, 3:1 CH2Cl2/DMSO) is added dropwise. The resulting mixture is stirred 5 minutes then Et3N added (15 mL, 108 mmol) in one portion. The cold bath is removed and stirring continued for 15 minutes. The reaction mixture is then diluted with ethyl acetate, washed with water and then brine, dried over MgSO4 and concentrated. The crude, orange solid product is used without further purification.

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