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

HRID 8469

Reaktionsgleichung

Reaktionsgleichung von HRID 8469
[F:1][C:2]1[C:12]([F:13])=[C:11]([F:14])[CH:10]=[CH:9][C:3]=1[NH:4][C@@H:5]([CH3:8])[CH2:6][OH:7].C(O[CH:18]=[C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])C.C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC.ClCCl>[F:1][C:2]1[C:12]([F:13])=[C:11]([F:14])[CH:10]=[CH:9][C:3]=1[N:4]([CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C@@H:5]([CH3:8])[CH2:6][OH:7]

Komponenten

6

Edukt 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanol

Produkt 1

HCID 11485652Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonateAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80021Tetrahexylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound (103 mg) obtained in Example 51, diethyl ethoxymethylenemalonate (108 mg) and tetrahexylammonium chloride (29 mg) were dissolved in dichloromethane (1 ml). After adding potassium carbonate (138 mg), the mixture was stirred at room temperature for 22 hours. After the completion of the reaction, the residue was filtered off and the solvent was evaporated. Then the residue thus obtained was subjected to silica gel column chromatography to thereby give 147 mg (78%) of the title compound as a colorless solid. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 63.

Aufarbeitung

  1. customAfter the completion of the reaction
  2. filtrationthe residue was filtered off
  3. customthe solvent was evaporated
  4. customThen the residue thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-05a1c88e83fc4495b20a55fb1c3be8ed
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087778B2

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