Acetic Acid → 2-Methoxyethyl 2-acetyl-3-(2,4-difluorophenyl)-2-propenoate

HRID 987007

Reaktionsgleichung

Reaktionsgleichung von HRID 987007
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:17][CH2:18][CH2:19][O:20][CH3:21])(=[O:16])[CH2:12][C:13]([CH3:15])=[O:14].N1CCCCC1.C(O)(=O)C>C(O)(C)C>[C:13]([C:12](=[CH:4][C:3]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:2]=1[F:1])[C:11]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[O:16])(=[O:14])[CH3:15]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 737702,4-DifluorobenzaldehydeHCID 897342-Methoxyethyl acetoacetate

Produkt 1

HCID 543348912-Methoxyethyl 2-acetyl-3-(2,4-difluorophenyl)-2-propenoateAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

5.0 g (35 mmol) of 2,4-difluorobenzaldehyde are dissolved in 100 ml of isopropanol with 5.7 g (35 mmol) of 2-methoxyethyl acetoacetate. A freshly prepared solution of 1.0 ml of piperidine and 0.5 ml of glacial acetic acid in 5 ml of isopropanol is added to this solution and it is stirred overnight at 40° C. The mixture is concentrated, the residue is taken up in toluene, the solution is concentrated again and the residue is purified by filtration on 100 ml of silica gel (eluent: toluene/ethyl acetate 100:1) to give 5 g of the target compound as a yellow oil which is immediately reacted further.

Aufarbeitung

  1. concentrationThe mixture is concentrated
  2. concentrationthe solution is concentrated again
  3. filtrationthe residue is purified by filtration on 100 ml of silica gel (eluent: toluene/ethyl acetate 100:1)

Quellen und Nachweise

ORD-Eintrag
ord-5c514f623e7d418ba1dfdce3b83ddd22
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630494B2

Verknüpfte Notizen

Wird geladen…