Dimethyl Sulfoxide → 4-(4-Nitrophenyl)butanal

Participants

Reaction Conditions

Reaction Steps

To a cooled solution (−70° C.) of oxalyl chloride (2.0 M in CH2Cl2, 14.1 mL, 28.2 mmol), dimethylsulfoxide (DMSO) (4.40 g, 56.32 mmol) in CH2Cl2 (20 mL) was added dropwise. The resulting reaction mixture was then stirred for 30 minutes at −70° C. under a nitrogen atmosphere. A solution of 4-(4-nitrophenyl)butan-1-ol (5.00 g, 25.6 mmol) in CH2Cl2 (3 mL) was added dropwise, and the reaction mixture was stirred for 1 hour at −70° C. Et3N (16 mL, 115 mmol) was added, and the reaction mixture was then allowed to gradually warm to room temperature and stir for 30 minutes. The mixture was then quenched with H2O and extracted with EtOAc. The organic layers were washed with 0.1N HCl solution, H2O, brine, dried (Na2SO4), filtered, and concentrated in vacuo to give a lightly brown oil. Purification by flash chromatography (silica gel, 50% EtOAc/hexane) yielded 3.20 g (16.56 mmol, 65%) of the desired product.

Provenance & Evidence