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

HRID 885373
Notes
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Reaction equation

HRID 885373 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[CH2:22]Br)[CH:7]=1)[CH3:2].[O:25]1[CH2:29][C:28](=O)[N:27]=[C-:26]1.[H-].[Na+].[O:33]1CCOCC1>>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[CH2:22][N:27]2[CH2:28][CH2:29][O:25][C:26]2=[O:33])[CH:7]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 312751,4-DioxaneHCID 532495662H-1,3-oxazol-2-id-4-oneHCID 58237456[3-(2-Bromomethyl-4-chloro-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester

Product 1

HCID 58237617{3-[4-Chloro-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid ethyl ester

Conditions

Temperature
80 °C

Procedure

[3-(2-Bromomethyl-4-chloro-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester (0.15 g, 0.36 mmol), 2-oxazolidone (0.063 g, 0.72 mmol), and sodium hydride (60% in mineral oil; 0.03 g, 0.72 mmol) were combined in 1,4-dioxane (10 mL) and stirred at 80° C. for 2 hours. The mixture was cooled to room temperature to give the title compound, which was used directly as a crude solution in the hydrolysis step.

Workup

  1. temperatureThe mixture was cooled to room temperature

Sources & evidence

ORD record
ord-16004f9eb3a44caf93a3b1083b78ff83
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08242145B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes