N-Hydroxyphthalimide → 2-(2-Phenylethoxy)-1H-isoindole-1,3(2H)-dione

HRID 1647181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647181
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C([O-])(=O)C.[Na+].Cl[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CS(C)=O>[C:21]1([CH2:20][CH2:19][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 10665N-HydroxyphthalimideHCID 2314961-Chloro-2-phenylethaneHCID 517045Sodium Acetate

Produkt 1

HCID 30290092-(2-Phenylethoxy)-1H-isoindole-1,3(2H)-dioneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

N-Hydroxyphthalimide (15.0 g, 92 mmol) and sodium acetate (7.5 g, 92 mmol) were stirred in dimethylsulfoxide (70 ml) at ambient temperature for 3 h. 2-Chloroethylbenzene (12.5 g, 89 mmol) was added and the reaction mixture was heated at reflux for 2 h. After cooling and standing overnight the reaction mixture was filtered and the flitrate was poured onto ice/water (300 ml). The mixture was extracted with dichloromethane (4×100 ml), the combined extracts were dried (MgSO4) and evaporated in vacuo to a residue. Purification by flash chromatography on a silica gel column eluting with heptane/ethyl acetate (1/1) afforded the title compound as a colourless foam (15.7 g, 33%); 1H NMR (DMSO-d6)γ 3.05 (2H, t, --OCH2 --), 4.39 (2H, t, --CH2Ph), 7.20-7.35 (5H, m, Ar-H), 7.85 (4H, s, Ar-H).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. additionthe flitrate was poured onto ice/water (300 ml)
  6. extractionThe mixture was extracted with dichloromethane (4×100 ml)
  7. dry with materialthe combined extracts were dried (MgSO4)
  8. customevaporated in vacuo to a residue
  9. customPurification by flash chromatography on a silica gel column
  10. washeluting with heptane/ethyl acetate (1/1)

Quellen und Nachweise

ORD-Eintrag
ord-dcb7074ecd3c4cb39f735dfb6abd7808
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05430027

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