Phthalimide → Methyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)benzoate

HRID 1762169

Reaktionsgleichung

Reaktionsgleichung von HRID 1762169
Br[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.[K].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12>CN(C)C=O>[CH3:12][O:11][C:9]([C:8]1[CH:13]=[CH:14][C:5]([O:4][CH2:3][CH2:2][N:20]2[C:19](=[O:21])[C:18]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]3[C:16]2=[O:26])=[CH:6][CH:7]=1)=[O:10]

Komponenten

5

Edukt 3

HCID 6809PhthalimideHCID 1898264Methyl 4-(2-bromoethoxy)benzoateHCID 5462222Potassium

Produkt 1

HCID 7679064Methyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)benzoateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl 4-(2-Bromoethoxy)benzoate (126.52 g) and 99.5 g of potassium salt of phthalimide were dissolved in 600 ml of N,N-dimethylformamide and the solution was stirred at 78°-80° C. for 2 hours. The reaction solution was poured over ice water and extracted with chloroform. The chloroform layer was washed with water twice, dried with anhydrous magnesium sulphate, and concentrated in vacuo whereupon the residue was crystallised. Ether was added to the residue and filtered to give crystals in 149.23 g (yield: 94%). M.p. 129°-130.5° C.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with water twice
  3. dry with materialdried with anhydrous magnesium sulphate
  4. concentrationconcentrated in vacuo whereupon the residue
  5. customwas crystallised
  6. additionEther was added to the residue
  7. filtrationfiltered
  8. customto give crystals in 149.23 g (yield: 94%)

Quellen und Nachweise

ORD-Eintrag
ord-89aa20710e4e4a8c8ff3c0d15ac04285
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04831055

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