Sodium hydride → {3-[4-Bromo-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-5-chloro-phenyl}-acetic acid ethyl ester

HRID 885375

Reaktionsgleichung

Reaktionsgleichung von HRID 885375
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=2[CH2:21]Br)[CH:7]=1)[CH3:2].[O:24]1[CH2:28][C:27](=O)[N:26]=[C-:25]1.[H-].[Na+].[O:32]1CCOCC1>>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=2[CH2:21][N:26]2[CH2:27][CH2:28][O:24][C:25]2=[O:32])[CH:7]=1)[CH3:2]

Komponenten

5

Edukt 4

HCID 24758Sodium hydrideHCID 312751,4-DioxaneHCID 532495662H-1,3-oxazol-2-id-4-oneHCID 58237642[3-(4-Bromo-2-bromomethyl-phenoxy)-5-chloro-phenyl]-acetic acid ethyl ester

Produkt 1

HCID 58237451{3-[4-Bromo-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-5-chloro-phenyl}-acetic acid ethyl ester

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

[3-(4-Bromo-2-bromomethyl-phenoxy)-5-chloro-phenyl]-acetic acid ethyl ester (0.10 g, 0.25 mmol), 2-oxazolidone (0.044 g, 0.5 mmol), and sodium hydride (60% in mineral oil; 0.02 g, 0.5 mmol) were combined in 1,4-dioxane (4 mL) and stirred at 80° C. for 2 hours. After work-up, the crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound.

Aufarbeitung

  1. customAfter work-up, the crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2c8ac0ce5c634bb8833e87d1e8c9786b
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242145B2

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