1,3-Diethyl 2-oxopropanedioate → Ethyl 2-ethoxycarbonyl-4-(3-fluoro-4-methylphenyl)-2-hydroxy-4-oxobutanoate

HRID 7909

Reaktionsgleichung

Reaktionsgleichung von HRID 7909
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[CH3:8].[O:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>>[CH2:17]([O:16][C:14]([C:13]([OH:12])([CH2:10][C:9]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([F:1])[CH:3]=1)=[O:11])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:15])[CH3:18]

Komponenten

3

Edukt 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 27745691-(3-Fluoro-4-methylphenyl)ethan-1-one

Produkt 1

HCID 21991669Ethyl 2-ethoxycarbonyl-4-(3-fluoro-4-methylphenyl)-2-hydroxy-4-oxobutanoateAusbeute 79,3 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 3′-fluoro-4′-methylacetophenone (4.92 g, 32.3 mmol) and diethyl ketomalonate (6.19 g, 35.6 mmol) was stirred at 120° C. for 48 hours. The temperature of the reaction mixture was allowed to drop back to room temperature, and the mixture was purified by column chromatography on silica gel [silica gel 100 g, chloroform/ethyl acetate (10/1)] to yield the title compound as yellow crystals (8.41 9, 79.3%).

Aufarbeitung

  1. customto drop back to room temperature
  2. customthe mixture was purified by column chromatography on silica gel [silica gel 100 g, chloroform/ethyl acetate (10/1)]

Quellen und Nachweise

ORD-Eintrag
ord-592233984b9b4dd7b002c45f0958065b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087606B2

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