Water → HCID 178500902, Verbindung

HRID 50101

Reaktionsgleichung

Reaktionsgleichung von HRID 50101
[C:1]([CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].[F:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.[Sn](Cl)(Cl)(Cl)Cl.O>C1(C)C=CC=CC=1.C(OCC)(=O)C.CCCCCC>[NH2:17][C:16](=[C:6]([C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[C:7]([O:9][CH3:10])=[O:8])[C:15]1[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 145174-FluorobenzonitrileHCID 24287Tin tetrachlorideHCID 2759969Methyl 4-methyl-3-oxopentanoate

Produkt 1

HCID 178500902HCID 178500902, VerbindungAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

22.53 g of methyl isobutyrylacetate (0.15 mol, concentration 96%) and 18.54 g of 4-fluorobenzonitrile (0.15 mol, concentration 98%) were dissolved in 150 ml of toluene and treated with 43.32 g of tin tetrachloride (0.165 mol, concentration 99%) at room temperature over the course of 12 min. After half an hour at room temperature, the mixture was heated to 80° C. After 3 h, the suspension was cooled to room temperature and treated with 150 ml of water. It was diluted with 100 ml of ethyl acetate and the phases were separated. After extraction of the aqueous phase with ethyl acetate (2×100 ml), the combined organic phases were washed with 100 ml of saturated aqueous sodium hydrogencarbonate solution, and 100 ml of 1N sodium hydroxide solution and dried over magnesium sulphate. After concentration in vacuo, 46.46 g of crude product were obtained in the form of a yellowish solid. The solid was dissolved in a mixture of 50 ml of n-hexane and 5 ml of toluene under reflux and filtered hot. The product precipitated from the filtrate on cooling. By filtering through a frit and washing the filter cake with 2×40 ml of n-hexane, 32.42 g of methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate were obtained in the form of a spectroscopically pure solid.

Aufarbeitung

  1. waitAfter half an hour at room temperature
  2. temperaturethe suspension was cooled to room temperature
  3. customthe phases were separated
  4. extractionAfter extraction of the aqueous phase with ethyl acetate (2×100 ml)
  5. washthe combined organic phases were washed with 100 ml of saturated aqueous sodium hydrogencarbonate solution, and 100 ml of 1N sodium hydroxide solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationAfter concentration in vacuo
  8. custom46.46 g of crude product were obtained in the form of a yellowish solid
  9. temperatureunder reflux
  10. filtrationfiltered hot
  11. customThe product precipitated from the filtrate
  12. temperatureon cooling
  13. filtrationBy filtering through a frit
  14. washwashing the filter cake with 2×40 ml of n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-5e981c45b23e4be98159c0fce2877e2a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710178B2

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