Sodium hydride → HCID 58237522, compound

HRID 885231Notes

Reaction equation

HRID 885231 reaction equation
[O:1]1[CH2:5][C:4](=O)[N:3]=[C-:2]1.[H-].[Na+].[CH2:9]([O:11][C:12](=[O:30])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[CH2:28]Br)[CH:15]=1)[CH3:10].[O:31]1CCOCC1>>[CH2:9]([O:11][C:12](=[O:30])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[CH2:28][N:3]2[CH2:4][CH2:5][O:1][C:2]2=[O:31])[CH:15]=1)[CH3:10]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 312751,4-Dioxane2×HCID 532495662H-1,3-oxazol-2-id-4-oneHCID 58237529HCID 58237529, compound

Product 1

HCID 58237522HCID 58237522, compound

Procedure

To 2-oxazolidone (0.12 g, 1.4 mmol) in 1,4-dioxane (10 mL) was added sodium hydride (60% in mineral oil; 0.06 g, 1.5 mmol), and the mixture was stirred for 10 minutes. [3-(2-Bromomethyl-4-fluoro-phenoxy)-phenyl]-acetic acid ethyl ester (0.35 g, 0.95 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 (0.16 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-2c90aef5bcb7435dbc6988d6c5a4f810
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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