Water → 6-Ethoxypyridine-2-carbaldehyde

Temperature

-60 °C

DMSO (0.50 mL, 6.4 mmol) in CH2Cl2 (10 mL) was added dropwise to a solution of oxalyl chloride (2M in CH2Cl2, 3.1 mL, 6.1 mmol) in CH2Cl2 (20 mL) at −60° C. The resulting mixture was stirred at −60° C. for 10 minutes. (6-Ethoxy-pyridin-2-yl)-methanol (0.85 g, 5.6 mmol) in CH2Cl2 (5 mL) and DMSO (4 mL) was added dropwise. The mixture was stirred at −60° C. for 3 h, and was then allowed to warm to −20° C. and Et3N (6 mL) was added. The resulting solution was stirred at ambient temperature for 40 minutes. Water was added and the mixture was extracted with CH2Cl2. The organic phase was washed with brine, dried (Na2SO4), and concentrated. Diethyl ether was added to the residue and insoluble material was removed by filtration. The filtrate was concentrated to yield the title compound (0.60 g) in 70% yield as a solid. This crude product was used in the next step without further purification.

1. stirringThe mixture was stirred at −60° C. for 3 h
2. temperatureto warm to −20° C.
3. stirringThe resulting solution was stirred at ambient temperature for 40 minutes
4. extractionthe mixture was extracted with CH2Cl2
5. washThe organic phase was washed with brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated
8. additionDiethyl ether was added to the residue and insoluble material
9. customwas removed by filtration
10. concentrationThe filtrate was concentrated

ORD record

ord-5f566f96b7594723a5be6016d3d721d6

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859568B2