Dimethyl Sulfoxide → 1-(2-Fluoro-3-pyridinyl)-1-propanone

To a mixture of 1-(2-fluoropyridin-3-yl)propan-1-ol (12.3 g), dimethyl sulfoxide (130 mL) and triethylamine (65 mL) was added a sulfur trioxide-pyridine complex (25.6 g), and the mixture was stirred at room temperature for 14 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1) to give the title compound as a brown oil (yield 10.6 g, 87%).

1. additionwas added a sulfur trioxide-pyridine complex (25.6 g)
2. extractionthe mixture was extracted with ethyl acetate
3. washThe extract was washed with water and saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1)

ORD record

ord-6f0881e7436f4b4a9cad9d77878de15f

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933105B2