Sodium hydride → 4-[2-[[1,1'-Biphenyl]-2-yl]-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester

HRID 2225845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2225845
[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+].[C:16]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:25])[CH2:23]Br>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][CH2:23][C:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 127478451-([1,1'-Biphenyl]-2-yl)-2-bromoethan-1-one

Produkt 1

HCID 539437794-[2-[[1,1'-Biphenyl]-2-yl]-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl esterAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

4-Hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.721 g) in dimethylformamide (8 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 30 minutes and then 1-[1,1'-biphenyl]-2-yl-2-bromoethanone (1.1 g) in dimethylformamide (4 mL). The mixture was stirred at room temperature overnight and worked up as in Example 20. The residual oil (1.5 g) was purified by flash chromatography over silica gel (dichloromethane) to afford of 0.62 g of 4-[2-[[1,1'-biphenyl]-2-yl]-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester as an oil.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe residual oil (1.5 g) was purified by flash chromatography over silica gel (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-381719996dc64f48bf5776250ca76c95
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05344843

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