Dimethyl Sulfoxide → 4-(4-Nitrophenyl)butanal

Temperature

-70 °C

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.

1. customThe resulting reaction mixture
2. stirringthe reaction mixture was stirred for 1 hour at −70° C
3. temperatureto gradually warm to room temperature
4. stirringstir for 30 minutes
5. customThe mixture was then quenched with H2O
6. extractionextracted with EtOAc
7. washThe organic layers were washed with 0.1N HCl solution, H2O, brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give a lightly brown oil
12. customPurification by flash chromatography (silica gel, 50% EtOAc/hexane)

ORD record

ord-d0bc98fbdecf45cdbee15e96efca5254

Source dataset

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06972287B1