Dimethyl Sulfoxide → 6-Methyl-3-pyridinecarboxaldehyde

To a solution of oxalyl chloride (2 M in dichloromethane, 9.34 mL, 18.68 mmol) in 30 mL dichloromethane at −60° C. under argon, dimethyl sulfoxide (3.1 g, 2.81 mL, 39.63 mmol) was added over 20 min. The mixture was stirred at −60° C. for 20 min before a solution of (6-methylpyridin-3-yl)methanol in 8 mL dichloromethane was added over 20 min. The reaction mixture was stirred for 20 min, and then triethylamine (8.02 g, 11.05 mL, 79.25 mmol) was added over 10 min. The reaction mixture was allowed to warm up to room temperature and 48 mL water was added. The mixture was extracted with dichloromethane and the combined extracts were dried (Na2SO4), filtered and concentrated. The crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes) to isolate 1.67 g (85%) of the title compound as a light brown oil. HPLC: retention time=0.19 min.

1. additionwas added over 20 min
2. extractionThe mixture was extracted with dichloromethane
3. dry with materialthe combined extracts were dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes)

ORD record

ord-845caf940aa24907b69214c9644df0e4

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07452892B2