Diethyl Oxalate → 4,5-Dihydro-5,8-dimethyl-4-oxopyrano[3,2-b]indole-2-carboxylic acid

HRID 46731

Reaktionsgleichung

Reaktionsgleichung von HRID 46731
[CH3:1][C:2]([C:4]1[N:5]([CH3:15])[C:6]2[C:11]([C:12]=1[OH:13])=[CH:10][C:9]([CH3:14])=[CH:8][CH:7]=2)=[O:3].[Na].[C:17](OCC)(=O)[C:18]([O:20]CC)=[O:19].[Na][Na]>C(O)C>[CH3:15][N:5]1[C:6]2[CH:7]=[CH:8][C:9]([CH3:14])=[CH:10][C:11]=2[C:12]2[O:13][C:17]([C:18]([OH:20])=[O:19])=[CH:1][C:2](=[O:3])[C:4]1=2

Komponenten

6

Edukt 4

HCID 7268Diethyl OxalateHCID 141233DisodiumHCID 5360545SodiumHCID 125113281,5-dimethyl-3-hydroxy-1H-indol-2-yl methyl ketone

Produkt 1

HCID 126284314,5-Dihydro-5,8-dimethyl-4-oxopyrano[3,2-b]indole-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In a manner analogous to that of Example 14, 8.2 g (0.040 mole) of 1,5-dimethyl-3-hydroxy-1H-indol-2-yl methyl ketone (Example 12) was reacted with sodium metal (3.7 g, 0.16 mole) and diethyl oxalate (21.5g, 0.20 mole) in 200 ml absolute ethanol. The red disodium salt intermediate was then converted to the title compound as described in Example 17. Two recrystallization of the final product from DMF-water yielded yellow needles of mpt. 290°.

Quellen und Nachweise

ORD-Eintrag
ord-9977afb92eca43458dada9068c15f795
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175083

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