Potassium Carbonate → Diethyl 2-(indol-4-yloxy)malonate

HRID 16566

Reaktionsgleichung

Reaktionsgleichung von HRID 16566
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C(=O)([O-])[O-].[K+].[K+].[Br:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[Br:17][C:18]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20].[NH:6]1[C:7]2[C:3](=[C:2]([O:1][CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 754211H-indol-4-ol

Produkt 2

HCID 11608989Diethyl 2-(indol-4-yloxy)malonateAusbeute 34 %HCID 11639270Diethyl 2-bromo-2-(indol-4-yloxy)malonateAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

A solution of 4-hydroxyindole (266 mg, 2 mmol) in acetone (20 mL) was cooled to 0° C. under nitrogen and anhydrous potassium carbonate (414 mg, 3 mmol) was added. A solution of freshly distilled pure diethyl bromomalonate (574 mg, 2.4 mmol) in acetone (20 mL) was added dropwise and the mixture was stirred at room temperature overnight. Work up and flash chromatography as above afforded 7 (101 mg, 13%) and 8 (199 mg, 34%).

Quellen und Nachweise

ORD-Eintrag
ord-0c9a0cdfc8304382bf05447a70154c88
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737169B2

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