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

HRID 1171777ノート

反応式

HRID 1171777 の反応式
[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]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 24007Selenium Dioxide2 回HCID 670684753-(2-Ethoxyethoxy)-2-methylpyridine

生成物 1

HCID 866231293-(2-Ethoxyethoxy)pyridine-2-carbaldehyde収率 39%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bdc6f124716249fc8b6ef53bbf917b43
出典データセット
uspto-grants-2010_11
特許番号
US07829707B2

反応ノート

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