Triphenylphosphine → 6-(2-morpholine-4-yl ethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amide

HRID 17886

Reaktionsgleichung

Reaktionsgleichung von HRID 17886
[CH:1]([NH-:4])([CH3:3])[CH3:2].[OH:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:11]([C:16]([O-:18])=[O:17])[C:12]2=[O:15])=[CH:8][CH:7]=1.O[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.C1C=CC=CC=1>[CH:1]([NH-:4])([CH3:3])[CH3:2].[N:28]1([CH2:27][CH2:26][O:5][C:6]2[CH:14]=[C:13]3[C:9]([C:10]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[C:11]([C:16]([O-:18])=[O:17])[C:12]3=[O:15])=[CH:8][CH:7]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178458041HCID 178458041, Verbindung

Produkt 1

HCID 866140296-(2-morpholine-4-yl ethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amide (7.0 g, 22.78 mmol) was dissolved in tetrahydrofuran:benzene (150 ml:50 ml). Then, hydroxyethylmorpholine (3.59 g, 27.33 mmol) and triphenyl phosphine (7.17 g, 27.33 mmol) were added thereto. When the temperature was adjusted to 0° C., diisopropyl azodicarboxylate (5.53 g, 27.33 mmol) was added dropwise to the mixture followed by stirring for 2 hours at room temperature. The mixture was washed with brine and extracted with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 6-(2-morpholine-4-yl ethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amide (9.5 g, yield 99%).

Aufarbeitung

  1. customwas adjusted to 0° C.
  2. washThe mixture was washed with brine
  3. extractionextracted with ethyl acetate
  4. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customthe resulting residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5da6139b69b8451d84463995d522f076
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741323B2

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