Cesium carbonate → Ethyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(2-hydroxyethoxy)benzoate

HRID 2177700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2177700
Br[CH2:2][CH2:3][OH:4].[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([OH:26])[C:18]([C:27]3[CH:31]=[CH:30][O:29][CH:28]=3)=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([O:26][CH2:2][CH2:3][OH:4])[C:18]([C:27]3[CH:31]=[CH:30][O:29][CH:28]=3)=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonate2×HCID 108982-Bromoethanol4×HCID 67107629Ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoate2×

Produkt 1

HCID 67107477Ethyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(2-hydroxyethoxy)benzoateAusbeute 33,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 2-bromoethanol (0.034 g) in DMF (1 ml) was added to a stirred mixture of ethyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate (Intermediate 36, 0.1 g) and cesium carbonate (0.127 g) in DMF (1 ml). The resultant mixture was stirred at room temperature for 3 hours. Further 2-bromoethanol (0.017 g) was added and the mixture was stirred at room temperature for a further 3 days. Cesium carbonate (0.085 g) and 2-bromoethanol (0.024 g) were added and the mixture was stirred for 1 hour. 2-Bromoethanol (0.015 g) was added and the mixture was stirred for a further 1 hour. The resultant mixture was partitioned between ethyl acetate and water and the aqueous layer was further extracted with ethyl acetate. The combined organic layers were washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 30-50%. The product was again purified by chromatography on silica, eluting with a mixture of ethyl acetate and pentane with a gradient of 25-30% to give ethyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(2-hydroxyethoxy)benzoate (0.037 g) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred for 1 hour
  2. stirringthe mixture was stirred for a further 1 hour
  3. customThe resultant mixture was partitioned between ethyl acetate and water
  4. extractionthe aqueous layer was further extracted with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography on silica
  10. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 30-50%
  11. customThe product was again purified by chromatography on silica
  12. washeluting with a mixture of ethyl acetate and pentane with a gradient of 25-30%

Quellen und Nachweise

ORD-Eintrag
ord-49f7f654aedf4f72a4d237e5b29887d0
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067905B2

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