3,4-Dimethylpyridine → 1-(2-Furyl)-2-(3-methylpyridin-4-yl)ethanone

HRID 337528

반응식

HRID 337528 반응식
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](OCC)=[O:15].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[Cl-].[NH4+]>C1COCC1>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=[O:15])[CH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH3:1]

참가 물질

6

반응물 4

HCID 114173,4-DimethylpyridineHCID 11980Ethyl 2-furoateHCID 25517Ammonium ChlorideHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 231444431-(2-Furyl)-2-(3-methylpyridin-4-yl)ethanone수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3,4-Dimethylpyridine (2.25 mL, 20.0 mmol) and ethyl furan-2-carboxylate (5.02 mL, 40.0 mmol) were dissolved in THF (20 mL), and at 0° C., a 1.0 mol/L solution of lithium hexamethyldisilazide in THF (40.0 mL, 40.0 mmol) was added dropwise thereto, followed by stirring at room temperature for 1.5 hours. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed successively with a saturated aqueous solution of ammonium chloride and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:2) to afford 1-(2-furyl)-2-(3-methylpyridin-4-yl)ethanone (3.34 g, 16.6 mmol).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed successively with a saturated aqueous solution of ammonium chloride
  3. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:2)

출처 및 근거

ORD 기록
ord-d70083a2bb214931a9c315615149e280
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889718B2

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