Sodium hydride → HCID 19744869, Verbindung

HRID 1030728Notizen

Reaktionsgleichung

[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[C:12](=[O:23])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.[H-].[Na+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29]>CN(C)C=O>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[C:3]([C:12](=[O:23])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[C:2]([O:1][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Then, 30 ml of dimethylformamide was added to 5.0 g of 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-1-propanone and 420 mg of sodium hydride, and the mixture was stirred at 0° C. for 1 hour. Then, 2.6 g of methyl α-bromoacetate was added to the mixture, and the mixture was stirred at 0° C. for 1 hour and at room temperature for 1 hour to effect a reaction. After the reaction, the reaction mixture was extracted with ethyl acetate and filtered, and the solvent was removed from the filtrate by distillation. The obtained residue was subjected to the silica gel chromatography [230-400 mesh silica gel; eluting solvent=n-hexane/ethyl acetate (2/1)] and recrystallized from a mixed solvent of diethyl ether and n-hexane to obtain 5.3 g (yield=87.1%) of 1-(4,6-dimethoxy-2-methoxycarbonylmethoxyphenyl)-3-(4-methoxyphenyl)-1-propanone in the form of a colorless plate.

Aufarbeitung

stirringthe mixture was stirred at 0° C. for 1 hour and at room temperature for 1 hour
customa reaction
customAfter the reaction
extractionthe reaction mixture was extracted with ethyl acetate
filtrationfiltered
customthe solvent was removed from the filtrate by distillation
customrecrystallized from a mixed solvent of diethyl ether and n-hexane

Quellen und Nachweise

ORD-Eintrag: ord-6fec2c2de37948739d3efb1bb554a5ff
Quelldatensatz: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05106871

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