Iodoethane → Ethyl {3-chloro-4-[4-(ethyloxy)-9-hydroxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetate

HRID 913180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913180
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:20](=[O:21])[C:19]3[C:18]([OH:22])=[C:17]4[CH:23]=[CH:24][CH:25]=[CH:26][C:16]4=[C:15]([OH:27])[C:14]=3[C:13]2=[O:28])=[C:8]([Cl:29])[CH:7]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:38][CH3:39]>CC(C)=O>[Cl:29][C:8]1[CH:7]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:30])[CH:11]=[CH:10][C:9]=1[N:12]1[C:20](=[O:21])[C:19]2[C:18]([OH:22])=[C:17]3[CH:23]=[CH:24][CH:25]=[CH:26][C:16]3=[C:15]([O:27][CH2:38][CH3:39])[C:14]=2[C:13]1=[O:28]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178470686ethyl 2-[3-chloro-4-(4,9-dihydroxy-1,3-dioxobenzo[f]isoindol-2-yl)phenyl]acetate

Produkt 1

HCID 58012488Ethyl {3-chloro-4-[4-(ethyloxy)-9-hydroxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetateAusbeute 56,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of ethyl[3-chloro-4-(4,9-dihydroxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate (2.0 g, 4.70 mmol) in acetone (50 ml), was added potassium carbonate (0.656 g, 4.75 mmol) followed by iodoethane (0.38 ml, 4.75 mmol). This was heated at reflux for 24 hours. The solvent was evaporated and water added to the residue. The resulting gummy brown solid was collected by filtration and dried in the vacuum oven. This was purified using reverse phase chromatography to give the title compound (1.21 g, 2.67 mmol). LC/MS: Rt=3.66, [MH]+ 454.

Aufarbeitung

  1. temperatureThis was heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent was evaporated
  4. additionwater added to the residue
  5. filtrationThe resulting gummy brown solid was collected by filtration
  6. customdried in the vacuum oven
  7. customThis was purified

Quellen und Nachweise

ORD-Eintrag
ord-9709db605dec4f4f88fd037b91eb9eb1
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026270B2

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