Sodium hydride → 4-[[2-[4-(1,1'-Biphenyl)oxy]ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

HRID 2225661

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].S([O-])(=O)(=O)C.[C:21]1([C:27]2[CH:36]=[CH:35][C:30]([O:31][CH2:32][CH2:33]O)=[CH:29][CH:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:33][CH2:32][O:31][C:30]2[CH:35]=[CH:36][C:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:28][CH:29]=2)=[CH:7][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.724 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 15 minutes and treated with the mesylate of 2-(4-phenylphenoxy)ethanol (1.4 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The crude dichloromethane extract was purified by HPLC (dichloromethane-hexane; 4:1) and the resulting solids were crystallized from dichloromethane-diethyl ether to provide 0.45 g of 4-[[2-[4-(1,1'-biphenyl)oxy]ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester as an 0.25 molar hydrate, mp 143°-145° C.

Aufarbeitung

extractionThe crude dichloromethane extract
customwas purified by HPLC (dichloromethane-hexane; 4:1)
customthe resulting solids were crystallized from dichloromethane-diethyl ether

Quellen und Nachweise

ORD-Eintrag: ord-69de032075024fbea65339ce33ab9fd2
Quelldatensatz: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05344843

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