2-(Chloroethoxy)ethanol → 2-(2-(2-Hydroxyethoxy)ethyl)-1H-isoindole-1,3(2H)-dione

HRID 399579

Reaktionsgleichung

Reaktionsgleichung von HRID 399579
Cl[CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.[K]>CN(C)C=O>[C:8]1(=[O:18])[N:12]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7])[C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12

Komponenten

4

Edukt 2

HCID 123612-(Chloroethoxy)ethanolHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 27554062-(2-(2-Hydroxyethoxy)ethyl)-1H-isoindole-1,3(2H)-dioneAusbeute 64,17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 2-(2-chloroethoxy)ethanol 14 (5 mL, 47.4 mmol) in N,N-dimethylformamide (35 mL) was added potassium phthalimide 2 (8.8 g, 47.51 mmol), and the reaction mixture was stirred for 20 h at 70° C. The mixture was concentrated and then diluted with dichloromethane (300 mL), and the organic layer was washed with water, dried, and concentrated. The residue was purified by flash column chromatography (3:2 to 2:3 hexane-ethyl acetate) to give compound 15 as a white solid (7.15 g, 64.17%) having an RF of 0.12 (solvent 3:2 hexane-ethyl acetate). See FIG. 9.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additiondiluted with dichloromethane (300 mL)
  3. washthe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (3:2 to 2:3 hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-cf405ceb7bdf43ffb257a0be49cbc372
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05821356

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