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2-Chlorobenzaldehyde → Methyl 2-(2-chlorobenzylidene)-4,4-dimethoxy-3-oxovalerate

HRID 1248666
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1248666
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][O:11][C:12]([O:21][CH3:22])([CH3:20])[C:13](=[O:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16].N1CCCCC1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:14]([C:13](=[O:19])[C:12]([O:11][CH3:10])([O:21][CH3:22])[CH3:20])[C:15]([O:17][CH3:18])=[O:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 69962-ChlorobenzaldehydeHCID 8082PiperidineHCID 5076552Methyl 4,4-dimethoxy-3-oxopentanoate

Produkt 1

HCID 54451845Methyl 2-(2-chlorobenzylidene)-4,4-dimethoxy-3-oxovalerateAusbeute 112,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

A mixture of 2-chlorobenzaldehyde (2.81 g), methyl 4,4-dimethoxy-3-oxovalerate (3.81 g) and piperidine (0.2 ml) in benzene (20 ml) was refluxed under azeotropic dehydration for 7.5 hours. A small amount of benzene was added to the reaction mixture and the resultant solution was washed with water and dried over magnesium sulfate. The solvent was removed from the solution to give a reddish oil (7.04 g) of methyl 2-(2-chlorobenzylidene)-4,4-dimethoxy-3-oxovalerate. The mixture of the oily product (6.39 g) obtained above and methyl 3-aminocrotonate (2.33 g) was heated at 132° C. for 3.5 hours, allowed to stand and then dissolved in ethyl acetate. The resultant solution was washed with water and an aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent was removed from the solution under reduced pressure to give a viscous and brown oil (8.28 g). This oil was subjected to column chromatography on silica gel with an eluent (a mixture of 20 parts of benzene and one part of ethyl acetate by volume) to give an oily substance (5.26 g).

Aufarbeitung

  1. temperaturewas refluxed under azeotropic dehydration for 7.5 hours
  2. washthe resultant solution was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed from the solution

Quellen und Nachweise

ORD-Eintrag
ord-dd3ba350450145a9aacd57b7f0526331
Quelldatensatz
uspto-grants-1985_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04525478

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