Potassium Carbonate → HCID 21879099, Verbindung

HRID 724700

Reaktionsgleichung

Reaktionsgleichung von HRID 724700
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[C:12]=1[C:13]([O:15][CH3:16])=[O:14].[C:22](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.ClCCl>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:12]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:3][CH:4]=1)=[O:7]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 519869Methyl 2,6-dihydroxybenzoate

Produkt 1

HCID 21879099HCID 21879099, VerbindungAusbeute 9,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Fluorobenzaldehyde (1.00 g, 8.06 mmol) and methyl 2,6-dihydroxybenzoate (2.03 g, 12.1 mmol) were dissolved in N,N-dimethylformamide (50 mL) and potassium carbonate (1.11 g, 8.06 mmol) was added. The reaction was stirred at room temperature overnight. The reaction was diluted with water (25 mL) and the layers separated. The aqueous phase was extracted twice with ethyl acetate (25 mL) then twice with diethyl ether (50 mL). The organic phases were combined and dried over MgSO4. The solution was filtered and the solvent evaporated then placed under high vacuum. The mixture was chromatographed, eluted with 25–50% ethyl acetate/hexanes. The desired fractions were combined and concentrated to give a light yellow oil. The product was redissolved in a minimum amount of dichloromethane, triturated with hexane and the solvent evaporated to give an oily yellow solid (0.21 g, 9%). 1H NMR (400 MHz, CDCl3): δ 9.93 (s, 1H), 7.84 (m, 2H), 7.38 (t, J=8.4 Hz, 1H), 7.08 (m, 2H), 6.81 (d, J=8.3 Hz, 1H), 6.63 (d, J=8.2 Hz, 1H), 3.89 (s, 3H), 3.78 (s, 3H); LCMS found for C16H15O5 (M+H)+: m/z=287.0.

Aufarbeitung

  1. customthe layers separated
  2. extractionThe aqueous phase was extracted twice with ethyl acetate (25 mL)
  3. dry with materialdried over MgSO4
  4. filtrationThe solution was filtered
  5. customthe solvent evaporated
  6. customThe mixture was chromatographed
  7. washeluted with 25–50% ethyl acetate/hexanes
  8. concentrationconcentrated
  9. customto give a light yellow oil
  10. customtriturated with hexane
  11. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-3c4f12b22be746579ccad218621e36e8
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141596B2

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