Ethyl Acetate → 3-(2-Ethoxyethoxy)pyridine-2-carbaldehyde

Temperature

75 °C

A mixture of 3-(2-ethoxyethoxy)-2-methylpyridine (0.506 g, 2.79 mmol) and selenium dioxide (0.31 g, 2.79 mmol) in 1,4-dioxane (10 mL) was heated at 75° C. overnight. After cooling to r.t., the mixture was filtered and the solids were washed with ethyl acetate. The solvent was removed in vacuo. The reaction was not complete and the solid was dissolved in 1,4 dioxane (15 mL) and selenium dioxide (0.31 g, 2.79 mmol) was added. The mixture was heated at 110° C. overnight. Ethyl acetate (10 mL) was added and the mixture was filtered. The black solid was washed with ethyl acetate and the filtrate was evaporated in vacuo. The crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 100% ethyl acetate), obtaining 0.21 g (39%) of the title compound.

1. temperatureAfter cooling to r.t.
2. filtrationthe mixture was filtered
3. washthe solids were washed with ethyl acetate
4. customThe solvent was removed in vacuo
5. dissolutionthe solid was dissolved in 1,4 dioxane (15 mL)
6. temperatureThe mixture was heated at 110° C. overnight
7. filtrationthe mixture was filtered
8. washThe black solid was washed with ethyl acetate
9. customthe filtrate was evaporated in vacuo
10. customThe crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 100% ethyl acetate)

ORD record

ord-bdc6f124716249fc8b6ef53bbf917b43

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829707B2