Potassium Carbonate → 3-[4-[4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenyloxy]butyl]-1,5,5-trimethylimidazolidine-2,4-dione

HRID 1919764Notes

Reaction equation

HRID 1919764 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:22][CH2:23][O:24][CH3:25])([C:18]([F:21])([F:20])[F:19])[C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=1[CH2:26][CH2:27][CH3:28].[CH3:29][N:30]1[C:34]([CH3:36])([CH3:35])[C:33](=[O:37])[NH:32][C:31]1=[O:38].C(=O)([O-])[O-].[K+].[K+]>>[F:15][C:14]([F:17])([F:16])[C:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][N:32]2[C:33](=[O:37])[C:34]([CH3:36])([CH3:35])[N:30]([CH3:29])[C:31]2=[O:38])=[C:8]([CH2:26][CH2:27][CH3:28])[CH:9]=1)([O:22][CH2:23][O:24][CH3:25])[C:18]([F:21])([F:20])[F:19]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 812951,5,5-Trimethylimidazolidine-2,4-dioneHCID 592350954-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenyl 4-bromobutyl ether

Product 1

HCID 249910743-[4-[4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenyloxy]butyl]-1,5,5-trimethylimidazolidine-2,4-dioneYield 100%

Procedure

4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenyl 4-bromobutyl ether (70 mg, 0.15 mmol), 1,5,5-trimethylimidazolidine-2,4-dione (24.8 mg, 0.17 mmol) and potassium carbonate (31.1 mg, 0.23 mmol) were added, followed by stirring overnight at room temperature. The reaction solution was extracted with ethyl acetate-water, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel preparative thin-layer chromatography (hexane:ethyl acetate=3:1) to obtain 78.8 mg of the title compound (yield: 100%) as a colorless oil.

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate-water
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel preparative thin-layer chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-47403d99ccec46fba11a4ca97dc58158
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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