Sodium Hydroxide → HCID 57796788, Verbindung

HRID 1362557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362557
[OH-].[Na+].C[O:4][C:5](=[O:28])/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15](=[O:27])/[CH:16]=[CH:17]/[C:18]2[CH:26]=[CH:25][C:21]3[O:22][CH2:23][O:24][C:20]=3[CH:19]=2)[CH:9]=1>O1CCCC1>[O:22]1[C:21]2[CH:25]=[CH:26][C:18](/[CH:17]=[CH:16]/[C:15]([NH:14][C:10]3[CH:9]=[C:8](/[CH:7]=[CH:6]/[C:5]([OH:28])=[O:4])[CH:13]=[CH:12][CH:11]=3)=[O:27])=[CH:19][C:20]=2[O:24][CH2:23]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 577968743-[3-[[(E)-3-(1,3-Benzodioxol-5-yl)-1-oxo-2-propenyl]amino]phenyl]-(E)-2-propenoic acid methyl ester

Produkt 1

HCID 57796788HCID 57796788, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(Method G4) 1N NaOH solution (2.56 ml, 2.56 mmol) was added to a solution of 3-[3-[[(E)-3-(1,3-benzodioxol-5-yl)-1-oxo-2-propenyl]amino]phenyl]-(E)-2-propenoic acid methyl ester (3a) (0.30 g, 0.85 mmol) in tetrahydrofuran (4.0 ml), and the resultant mixture was stirred at ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was acidified with 2N HCl solution and extracted with ethyl acetate. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was washed with diethyl ether. The title compound was obtained as a white solid (0.24 g, 84%). 1H NMR (DMSO-d6, HMDSO), δ: 6.09 (2H, s); 6.43 (1H, d, J=16.0 Hz); 6.60 (1H, d, J=16.0 Hz); 6.89-7.76 (8H, m); 7.92 (1H, br s); 10.16 (1H, br s); 12.38 ppm (1H, br s).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with water, saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed
  6. washthe residue was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-61739be1d6b34d3d8f8f7b30fc750f22
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880020B2

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