Dimethyl Sulfoxide → 3-(Pyridin-3-yl)propanal

Temperature

-10 °C

A stirred solution of oxalyl chloride (1 ml) in dichloromethane (25 ml) under argon was cooled to -60° C. A solution of dimethylsulphoxide (1.7 ml) in dichloromethane (5 ml) was then added dropwise and the temperature maintained at <-50° C. After 2 minutes, a solution of 3-(3-pyridyl)propanol (1.37 g) in dichloromethane (10 ml) was added dropwise during 5 minutes. Stirring was continued for a further 15 minutes and then triethylamine (7.0 ml) was added dropwise. The mixture was allowed to warm to -10° C. and water (50 ml) was then added. The aqueous mixture was extracted with ether (1×100, 2×25 ml) and the combined extracts washed with saturated brine (2×25 ml), then dried (MgSO4) and evaporated. Flash chromatography of the residue, eluting with ethyl acetate, gave 3-(3-pyridyl)propionaldehyde, as a pale yellow oil (630 mg); NMR (90 MHz; CDCl3): 2.85 (4H, m), 7.16 (1H, m), 7.48 (1H, m), 8.40 (2H, m), 9.76 (1H, s).

1. temperaturethe temperature maintained at <-50° C
2. waitwas continued for a further 15 minutes
3. extractionThe aqueous mixture was extracted with ether (1×100, 2×25 ml)
4. washthe combined extracts washed with saturated brine (2×25 ml)
5. dry with materialdried (MgSO4)
6. customevaporated
7. washFlash chromatography of the residue, eluting with ethyl acetate

ORD record

ord-6ac41d3b6f454068a9815a19e822b7c3

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04921866