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) was added, dropwise, DMSO (3 mL). The resulting solution was stirred for 5 min then a solution of 4-[pyridin-4-yl]-benzyl alcohol (2.80 g, 15 mmol) (reference example 19a) in CH2Cl2/DMSO (27 mL, 3:1 CH2Cl2/DMSO) was added dropwise. The resulting mixture was stirred 5 min then Et3N added (15 mL, 108 mmol) in one portion. The cold bath was removed and stirring continued for 15 min. The reaction mixture was then diluted with ethyl acetate, washed with water and then brine, dried over MgSO4 and concentrated. The crude, orange solid product was used without further purification.

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