Potassium Carbonate → N-[4-chloro-3-(1-ethoxycarbonylpropen-1-yloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

HRID 485207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 485207
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[OH:19].Br[CH:21]([CH:27](Br)[CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[O:18])[C:10]3[CH2:17][CH2:16][CH2:15][CH2:14][C:11]=3[C:12]2=[O:13])=[CH:4][C:3]=1[O:19][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][CH3:28]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 98157Butanoic acid, 2,3-dibromo-, ethyl esterHCID 12769235N-(3-Hydroxy-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide

Produkt 1

HCID 56629888N-[4-chloro-3-(1-ethoxycarbonylpropen-1-yloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 4.0 g. of N-(4-chloro-3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide, 4.7 g. of ethyl 2,3-dibromobutyrate, 2.4 g. of potassium carbonate and 35 ml. of acetone was refluxed with stirring for 6 hours and the precipitated salt was separated by a filtration. The filtrate was concentrated under a reduced pressure and 2N-HCl was added to the residue to obtain a crude crystal. The product was washed with water and dried and purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 3:7) to obtain 5.2 g. of Compound No. 158 shown in Table 1.

Aufarbeitung

  1. additionA mixture of 4.0 g
  2. customthe precipitated salt was separated by a filtration
  3. concentrationThe filtrate was concentrated under a reduced pressure and 2N-HCl
  4. additionwas added to the residue
  5. customto obtain a crude crystal
  6. washThe product was washed with water
  7. customdried
  8. custompurified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 3:7)
  9. customto obtain 5.2 g

Quellen und Nachweise

ORD-Eintrag
ord-4765923566204778b644606cf986ab3a
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04536209

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