Water → 6-Ethoxypyridine-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence