5H-[1,3]Dioxolo[4,5-f]indole-6,7-dione → 3-(1-Methoxy-1-phenyl-methylidene)-5,6-methylenedioxy-2-indolinone

HRID 1007388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1007388
C([C:3](CC)(P(=O)([O-])[O-])[C:4]1(OC)[CH:9]=[CH:8][CH:7]=[CH:6][CH2:5]1)C.C[C:19](C)([O-:21])C.[K+].[CH2:24]1[O:35][C:34]2[CH:33]=[C:32]3[C:28]([C:29](=O)[C:30](=[O:36])[NH:31]3)=[CH:27][C:26]=2[O:25]1>CN(C)C=O>[CH3:19][O:21][C:3](=[C:29]1[C:28]2[C:32](=[CH:33][C:34]3[O:35][CH2:24][O:25][C:26]=3[CH:27]=2)[NH:31][C:30]1=[O:36])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 156528335H-[1,3]Dioxolo[4,5-f]indole-6,7-dioneHCID 23665647Potassium tert-butoxideHCID 86759531Diethyl-1-methoxybenzylphosphonate

Produkt 1

HCID 695646343-(1-Methoxy-1-phenyl-methylidene)-5,6-methylenedioxy-2-indolinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Under a nitrogen atmosphere 4.5 g of diethyl-1-methoxybenzylphosphonate (according to Burkhouse, D.; Zimmer, H.; Synthesis 1984, 330) are dissolved in 40 ml of absolute dimethylformamide and at −40° C. 4.0 g of potassium-tert-butoxide are added batchwise and stirred for 15 minutes at −10° C. 3.0 g of 5,6-methylenedioxyisatin (according to Lackey, K.; Sternbach, D. D.; Synthesis 1993, 993) are added to the clear solution and stirred for 1 hour at ambient temperature. After this time the mixture is poured into 20 ml of ice-cold saturated potassium hydrogen sulphate solution and extracted with ethyl acetate. The ethyl acetate phase is washed with water, dried over sodium sulphate and concentrated by evaporation. Finally the residue is separated through a silica gel column with toluene/ethyl acetate (5:1). The product obtained can be recrystallised from ether.

Aufarbeitung

  1. stirringstirred for 1 hour at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. customFinally the residue is separated through a silica gel column with toluene/ethyl acetate (5:1)
  7. customThe product obtained can
  8. custombe recrystallised from ether

Quellen und Nachweise

ORD-Eintrag
ord-b2b46c844f114b12aaca447e40a18e13
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06794395B1

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