N-(2-Hydroxyethyl)phthalimide → 2-Phthalimidoethyl acetoacetate

HRID 2372713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2372713
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[CH3:15][C:16]1[O:22]C(C)(C)O[C:18](=[O:19])[CH:17]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:18]([O:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14])(=[O:19])[CH2:17][C:16]([CH3:15])=[O:22]

Komponenten

5

Edukt 2

HCID 77499N-(2-Hydroxyethyl)phthalimideHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Produkt 1

HCID 114031062-Phthalimidoethyl acetoacetateAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 10.0 g (52.3 mmol) of N-(2-hydroxyethyl)phthalimide, 8.84 ml (67.7 mmol) of 2,2,6-trimethyl-1,3-dioxen-4-one, and 10 mg of p-toluenesulfonic acid in 50 ml of toluene is heated at reflux under N2 for 4 hr. The solvent is removed under vacuum and the dark-colored residue is flash chromatographed on silica gel (1:1 hexane-EtOAc). The resulting product is recrystallized from EtOAc to give 11.0 g of 2-phthalimidoethyl acetoacetate.

Aufarbeitung

  1. temperatureat reflux under N2 for 4 hr
  2. customThe solvent is removed under vacuum
  3. customchromatographed on silica gel (1:1 hexane-EtOAc)
  4. customThe resulting product is recrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-0c2d3b1d33dd46a381e1c6bb907c55ae
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05100892

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