2-Pentanone, 5-chloro- → 2-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dione

HRID 324597

Reaktionsgleichung

Reaktionsgleichung von HRID 324597
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Cl[CH2:14][CH2:15][CH2:16][C:17](=[O:19])[CH3:18]>CN(C=O)C>[O:19]=[C:17]([CH3:18])[CH2:16][CH2:15][CH2:14][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

Komponenten

4

Edukt 2

HCID 799932-Pentanone, 5-chloro-HCID 24194345Phthalimide potassium salt

Produkt 1

HCID 2362702-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dioneAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

24.59 g (132.8 mmol) of potassium phthalimide are added to a solution of 14.3 ml (124.4 mmol) of 5-chloro-2-pentanone in 100 ml of DMF and the mixture is left to stir at room temperature for 3 h and at 60° C. for 30 h. After filtering, the filtrate is partitioned between water and dichloromethane. The phases are separated and the organic phase is washed successively with water, twice with an 0.2N solution of NaOH and water and then dried over sodium sulfate. After filtering, the solvent is removed in vacuo and the residue is chromatographed through silica gel using heptane/ethyl acetate=6/4. 9.8 g (34%) of (14.1) are obtained after concentrating the product fractions.

Aufarbeitung

  1. waitthe mixture is left
  2. filtrationAfter filtering
  3. customthe filtrate is partitioned between water and dichloromethane
  4. customThe phases are separated
  5. washthe organic phase is washed successively with water, twice with an 0.2N solution of NaOH and water
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtering
  8. customthe solvent is removed in vacuo
  9. customthe residue is chromatographed through silica gel

Quellen und Nachweise

ORD-Eintrag
ord-27b91a525a8f4762a5363865f4505b8c
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218415B1

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