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

HRID 885226Notes

Reaction equation

HRID 885226 reaction equation
[O:1]1[CH2:5][C:4](=O)[N:3]=[C-:2]1.[H-].[Na+].[CH2:9]([O:11][C:12](=[O:29])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:27]Br)[CH:15]=1)[CH3:10].[O:30]1CCOCC1>>[CH2:9]([O:11][C:12](=[O:29])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:27][N:3]2[CH2:4][CH2:5][O:1][C:2]2=[O:30])[CH:15]=1)[CH3:10]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 312751,4-Dioxane2×HCID 532495662H-1,3-oxazol-2-id-4-oneHCID 58237656[3-(2-Bromomethyl-phenoxy)-phenyl]-acetic acid ethyl ester

Product 1

HCID 58237501{3-[2-(2-Oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid ethyl ester

Procedure

To 2-oxazolidone (0.083 g, 1.0 mmol) in 1,4-dioxane (10 mL) was added sodium hydride (60% in mineral oil; 0.041 g, 1.03 mmol), and the mixture was stirred for 10 minutes. [3-(2-Bromomethyl-phenoxy)-phenyl]-acetic acid ethyl ester (0.30 g, 0.86 mmol) was added in 1,4-dioxane, and the reaction was stirred for 1 hour at room temperature. After work-up, the crude material was purified by preparative HPLC to give the desired product (0.14 g).

Workup

  1. stirringthe reaction was stirred for 1 hour at room temperature
  2. customAfter work-up, the crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-f891240d88be45619c113cd787e2c2fe
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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