Ethyl Acetate → 3-(2-Ethoxyethoxy)pyridine-2-carbaldehyde
Reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([CH3:13])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].[Se](=O)=[O:15].C(OCC)(=O)C>O1CCOCC1>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([CH:13]=[O:15])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
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.
Workup
- temperatureAfter cooling to r.t.
- filtrationthe mixture was filtered
- washthe solids were washed with ethyl acetate
- customThe solvent was removed in vacuo
- dissolutionthe solid was dissolved in 1,4 dioxane (15 mL)
- temperatureThe mixture was heated at 110° C. overnight
- filtrationthe mixture was filtered
- washThe black solid was washed with ethyl acetate
- customthe filtrate was evaporated in vacuo
- customThe crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 100% ethyl acetate)
Sources & evidence
- ORD record
- ord-1353b5d05d954d19a31d3fe773a67420
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859568B2
Reaction notes
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