Water → 2-[2-(4-Chloro-phenyl)-cyclopropyl]-isoindole-1,3-dione

HRID 1916024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916024
[Na].S(NN=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)(C1C=CC(C)=CC=1)(=O)=O.[CH:22]([N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])=[CH2:23].O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH:14]2[CH2:23][CH:22]2[N:24]2[C:25](=[O:34])[C:26]3[C:27](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]2=[O:29])=[CH:20][CH:19]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 866384034-Chlorobenzaldehyde tosyl hydrazone sodium salt

Produkt 1

HCID 684102072-[2-(4-Chloro-phenyl)-cyclopropyl]-isoindole-1,3-dioneAusbeute 26,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 168478Rhodium acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 4-chlorobenzaldehyde tosyl hydrazone sodium salt (1.67 g, 5.05 mmol), benzyltriethylammoniumchloride (115 mg, 0.5 mmol), rhodium acetate (20 mg, 0.05 mmol) and N-vinylphtalimide (4.32 g, 25.0 mmol) in dry 1,4-dioxane (13 ml) was stirred for one day under nitrogen at room temperature. Water (35 ml) was added to the mixture and the aqueous phase was extracted three times with dichloromethane. The combined organic layers were dried over Na2SO4. Evaporation gave the crude material, which was purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 1:1). To afford 392 mg (26.3% of theory) of 2-[2-(4-chloro-phenyl)-cyclopropyl]-isoindole-1,3-dione in the form of a solid.

Aufarbeitung

  1. extractionthe aqueous phase was extracted three times with dichloromethane
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customEvaporation
  4. customgave the crude material, which
  5. customwas purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ff56d522faa54c379f2ff6866cf26c3e
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618023B2

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