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

HRID 8479
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 8479
[OH-].[K+].F[C:4]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:5]=1[NH:6][C@@H:7]([CH3:10])[CH2:8][OH:9].C(O[CH:20]=[C:21]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])C.O>[Cl-].C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC.CN(C=O)C>[F:16][C:13]1[CH:12]=[CH:11][C:5]2[N:6]([CH:20]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C@@H:7]([CH3:10])[CH2:8][O:9][C:4]=2[C:14]=1[F:15]
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Komponenten

7

Edukt 4

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonate2×HCID 14797Potassium Hydroxide2×HCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanol

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 80021Tetrahexylammonium chlorideKatalysator
HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

At room temperature, KOH (330 mg) and tetrahexylammonium chloride (190.1 mg) were dissolved in DMF (15 ml). After adding a solution (5 ml) of (2S)-2-(2,3,4-trifluoroanilino)propanol (1 g, 99.8% ee) and diethyl ethoxymethylenemalonate (2.09 g) in DMF, the mixture was stirred for 1 hour. Next, it was heated to 60° C. and a solution (5 ml) of KOH (330 mg) and diethyl ethoxymethylenemalonate (120 mg) in DMF was added thereto. The resultant mixture was stirred at the same temperature for 5 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, 1.37 g (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-ffa02a76540e496189594119513487f8
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07087778B2

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