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Water → Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate

HRID 8472
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 8472
[OH-].[K+].[F:3][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].[CH2:17]([O:19][C:20](=[O:31])[C:21](=[CH:27]OCC)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:18].O>[Cl-].C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC.CN(C=O)C>[F:3][C:4]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:5]=1[N:6]([CH:27]=[C:21]([C:20]([O:19][CH2:17][CH3:18])=[O:31])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C@@H:7]([CH3:10])[CH2:8][OH:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 14797Potassium HydroxideHCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanol

Produkt 1

HCID 11485652Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonateAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80021Tetrahexylammonium chlorideKatalysator
HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

At room temperature, potassium hydroxide (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 diethylethoxymethylenemalonate (2.09 g) in DMF, the resultant mixture was stirred for 1 hour. After adding water, the liquid reaction mixture was extracted with a solvent mixture of ethyl acetate and n-hexane (3:2). The organic layer was washed with water and dried over anhydrous magnesium sulfate. After evaporating the solvent, IPE was added to the obtained residue and the mixture was stirred at 0° C. for 1 hour. The crystals thus precipitated were collected by filtration and the moist product thus obtained was dried under reduced pressure. Thus, the title compound (1.65 g, 99.8% ee) was obtained as colorless crystals. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 63.

Aufarbeitung

  1. customthe liquid reaction mixture
  2. extractionwas extracted with a solvent mixture of ethyl acetate and n-hexane (3:2)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter evaporating the solvent, IPE
  6. additionwas added to the obtained residue
  7. customThe crystals thus precipitated
  8. filtrationwere collected by filtration
  9. customthe moist product thus obtained
  10. customwas dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ed8211677cac405d8fa028af6a5bb94f
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07087778B2

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