Dimethyl Sulfoxide → 5-Methanesulfonylpentanal

To a dichloromethane (15 ml) solution of 5-(methylsulfonyl)-1-pentanol (344 mg, 2.07 mmol), dimethylsulfoxide (0.441 ml, 6.21 mmol) and triethylamine (1.15 ml, 8.28 ml) was added a sulfur trioxide pyridine complex (659 mg, 4.14 mmol) at 0° C. and the mixture was stirred at room temperature for 3 hours. After the reaction mixture was washed with water, the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, and the fraction obtained from the ethyl acetate eluate was concentrated under reduced pressure, whereby the title compound (183 mg, 1.11 mmol, 54%) was obtained as a colorless oil.

1. washAfter the reaction mixture was washed with water
2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
3. filtrationAfter filtration
4. concentrationthe filtrate was concentrated under reduced pressure
5. customthe fraction obtained from the ethyl acetate eluate

ORD record

ord-9b5dab2b43f74bfcb8584aec2f045974

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399775B2