Tetrahydrofuran → 3-[3-[[(E)-3-(1,3-Benzodioxol-5-yl)-1-oxo-2-propenyl]amino]phenyl]-(E)-2-propenoic acid methyl ester

HRID 1362556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362556
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[CH:11][C:12](Cl)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.COC(=O)[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[CH:21]=1)=[CH2:19].[C:28]([O-:31])(O)=[O:29].[Na+].O1CCC[CH2:34]1>O>[CH3:34][O:31][C:28](=[O:29])/[CH:19]=[CH:18]/[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:12](=[O:13])/[CH:11]=[CH:10]/[C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)[CH:21]=1

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 516892Sodium BicarbonateHCID 534112793-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl chlorideHCID 57495369HCID 57495369, Verbindung

Produkt 1

HCID 577968743-[3-[[(E)-3-(1,3-Benzodioxol-5-yl)-1-oxo-2-propenyl]amino]phenyl]-(E)-2-propenoic acid methyl esterAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

(Method G3) A solution of 3-benzo[1,3]dioxol-5-yl-acryloyl chloride (2a) (0.41 g, 1.95 mmol) in tetrahydrofuran (8.0 ml) was added to a mixture of m-aminophenylacrylic acid methyl ester (0.35 g, 1.97 mmol) in tetrahydrofuran (12.0 ml) and NaHCO3 (0.25 g, 3.00 mmol) in water (7.0 ml), and the resultant solution was stirred at room temperature for one hour. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was chromatographed on silica gel with dichlormethane-methanol (40:1, v/v) as eluent. The obtained product was washed with diethyl ether to give the title compound (0.50 g, 71%). 1H NMR (DMSO-d6, HMDSO), δ: 3.73 (3H, s); 6.09 (2H, s); 6.49 (1H, d, J=16.0 Hz); 6.67 (1H, d, J=16.0 Hz); 6.89-7.83 (8H, m).; 7.98 (1H, br s); 10.23 ppm (1H, br s)

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 2N HCl
  3. washThe organic layer was washed successively with water, saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed
  6. customthe residue was chromatographed on silica gel with dichlormethane-methanol (40:1
  7. washThe obtained product was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-febceddb0ab648728b9279c04003ad7f
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880020B2

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