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Water → (S)-Diethyl (7,8-Difluoro-3-Methyl-3,4-Dihydro-2H-[1,4]Benzoxazin-4-Yl)Methylene-Malonate

HRID 8478
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 8478
[OH-].[K+].F[C:4]1[C:26]([F:27])=[C:25]([F:28])[CH:24]=[CH:23][C:5]=1[N:6]([CH:11]=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@@H:7]([CH3:10])[CH2:8][OH:9].C(OC=C(C(OCC)=O)C(OCC)=O)C.O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C=O)C>[CH2:16]([O:15][C:13](=[O:14])[C:12](=[CH:11][N:6]1[C:5]2[CH:23]=[CH:24][C:25]([F:28])=[C:26]([F:27])[C:4]=2[O:9][CH2:8][C@@H:7]1[CH3:10])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:17]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 14797Potassium HydroxideHCID 11485652Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate

Produkt 1

HCID 11089557(S)-Diethyl (7,8-Difluoro-3-Methyl-3,4-Dihydro-2H-[1,4]Benzoxazin-4-Yl)Methylene-Malonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Potassium hydroxide (180 mg) and benzyltrimethylammonium chloride (60.7 mg) were dissolved in DMF (15 ml) by heating to 60° C. and a solution (5 ml) of diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate (1 g, 99.8% ee) and diethyl ethoxymethylenemalonate (120 mg) in DMF was added thereto. The obtained mixture was stirred at the same temperature for 7 hours. After adding water, the liquid reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. After evaporating the solvent, the obtained residue was subjected to silica gel column chromatography. Thus, 899 mg (99.8% ee) of the title compound was obtained as a yellow oily substance. Various spectral data was identical with those described in Japanese Patent No. 2,769,174.

Aufarbeitung

  1. customthe liquid reaction mixture
  2. extractionwas extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customAfter evaporating the solvent

Quellen und Nachweise

ORD-Eintrag
ord-09aad72a49c54100a1770b7ca03a3bcc
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07087778B2

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