Dimethyl Sulfoxide → 6-Methyl-3-pyridinecarboxaldehyde

To a stirred solution of dimethyl sulfoxide (25.3 mL, 0.357 mol) and CH2Cl2 (600 mL) under nitrogen at −78° C. was slowly added oxalyl chloride (16 mL, 0.19 mol). After completion of the addition, the mixture was stirred for additional 10 min. To the resulting solution was added dropwise a solution of (6-methyl-3-pyridyl)methanol (20 g, 0.162 mol) in CH2Cl2 (10 mL), and then the mixture was stirred at −78° C. for 2.5 hr. Triethylamine (110 mL, 0.82 mol) was slowly added at −78° C. and then the mixture was slowly warmed to room temperature and stirred for another 1 hr. The mixture was treated with water and the aqueous phase was extracted with CH2Cl2 (3×500 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by silica gel column to afford the title compound.

1. customat −78° C.
2. additionAfter completion of the addition
3. stirringthe mixture was stirred at −78° C. for 2.5 hr
4. stirringstirred for another 1 hr
5. extractionthe aqueous phase was extracted with CH2Cl2 (3×500 mL)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by silica gel column

ORD record

ord-7931479ceda84867901984f1e6461015

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946439B2