4-Methylpyridine → 1-(2-Furyl)-2-pyridin-4-ylethanone

HRID 747141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747141
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13](OCC)=[O:14].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CCCCCC>O1CCCC1>[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13](=[O:14])[CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Komponenten

6

Edukt 4

HCID 79634-MethylpyridineHCID 8058HexaneHCID 11980Ethyl 2-furoateHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 227080301-(2-Furyl)-2-pyridin-4-ylethanoneAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-picoline (4.6 g, 49.4 mmol) and ethyl 2-furancarboxylate (7.7 g, 54.9 mmol) in tetrahydrofuran (40 ml) was dropwise added lithium bis(trimethylsilyl)amide (100 ml, 100 mmol) over 1 hour at 0° C. under an atmosphere of nitrogen gas, followed by stirring as it was for 2 hours. Hexane (140 ml) was added to the reaction mixture, and the resulting crystals were collected by filtration. The resulting crystals were dissolved in ethyl acetate and a saturated aqueous ammonium chloride solution. The organic layer was washed with a saturated aqueous ammonium chloride solution twice and brine, dried over anhydrous sodium sulfate and concentrated. Hexane was added to the residue, and the resulting precipitates were collected by filtration and washed with hexane, to give the title compound (6.5 g, 70%) as a pale yellow solid.

Aufarbeitung

  1. customover 1 hour
  2. customat 0° C.
  3. filtrationthe resulting crystals were collected by filtration
  4. dissolutionThe resulting crystals were dissolved in ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous ammonium chloride solution twice
  6. dry with materialbrine, dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. additionHexane was added to the residue
  9. customthe resulting precipitates
  10. filtrationwere collected by filtration
  11. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-01eb6ef7415243289a13e6eeb68a2f82
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396836B2

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