Potassium Carbonate → 2,5-Dimethylfuran-3-carboxylic Acid 2-Methoxyethoxymethyl Ester

HRID 723731

Reaktionsgleichung

Reaktionsgleichung von HRID 723731
[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][CH2:19][CH2:20][O:21][CH2:22]Cl>CN(C=O)C.O>[CH3:17][O:18][CH2:19][CH2:20][O:21][CH2:22][O:8][C:7]([C:6]1[CH:5]=[C:4]([CH3:10])[O:3][C:2]=1[CH3:1])=[O:9]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 694652,5-Dimethyl-3-furoic acidHCID 775901-(Chloromethoxy)-2-methoxyethane

Produkt 1

HCID 587458882,5-Dimethylfuran-3-carboxylic Acid 2-Methoxyethoxymethyl EsterAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 2 L round-bottomed flask equipped with a mechanical stirrer was charged with 2,5-dimethyl-3-furoic acid (81.0 g, 0.58 mol) and potassium carbonate (95.9 g, 0.69 mol) in DMF (500 mL). An ice bath was used to cool the reaction as 2methoxyethoxymethyl chloride (72.2 g, 0.58 mol) was added portionwise. The reaction was stirred for 5 h at rt. The mixture was then diluted with water (1.5 L) and extracted with EtOAc (2×600 mL). The combined organics were washed with water (2×900 mL) and saturated sodium chloride solution (1 L), dried over MgSO4, filtered and concentrated to afford compound 803A (103 g, 82%) as a yellow oil. 1H NMR(CDCl3): δ=6.23 (s, 1H), 5.47 (s, 1H), 3.84 (m, 2H), 3.56 (m, 2H), 3.38 (s, 3H), 2.51 (s, 3H) and 2.20 ppm (s, 3H).

Aufarbeitung

  1. customA 2 L round-bottomed flask equipped with a mechanical stirrer
  2. customAn ice bath was used
  3. temperatureto cool
  4. additionwas added portionwise
  5. extractionextracted with EtOAc (2×600 mL)
  6. washThe combined organics were washed with water (2×900 mL) and saturated sodium chloride solution (1 L)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-280e921f30e6419fafea1d67eba91f51
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141578B2

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