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

HRID 1171777노트

반응식

HRID 1171777 반응식
[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]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24007Selenium Dioxide2회HCID 670684753-(2-Ethoxyethoxy)-2-methylpyridine

생성물 1

HCID 866231293-(2-Ethoxyethoxy)pyridine-2-carbaldehyde수율 39%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
75 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bdc6f124716249fc8b6ef53bbf917b43
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829707B2

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