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

HRID 353209

Reaktionsgleichung

Reaktionsgleichung von HRID 353209
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[N:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](OCC)=[O:24].CCCCCC>O1CCCC1>[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](=[O:24])[CH2:17][C:14]1[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=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

In a nitrogen atmosphere, lithium bis (trimethylsilyl) amide (100 mL, 100 mmol) was added dropwise into 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) at 0° C. over 1 hour, followed by stirring as it was for 2 hours. Hexane (140 mL) was added to the reaction solution, and the resulting crystals were collected by filtration. The resulting crystals were dissolved in ethyl acetate and an aqueous saturated solution of ammonium chloride. The organic layer was washed with an aqueous saturated solution of ammonium chloride (×2) 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. filtrationthe resulting crystals were collected by filtration
  2. dissolutionThe resulting crystals were dissolved in ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated solution of ammonium chloride (×2) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionHexane was added to the residue
  7. customthe resulting precipitates
  8. filtrationwere collected by filtration
  9. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-44405439bb6c4ba681347cc4241f19f9
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06750232B2

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