Potassium Carbonate → HCID 14678342, compound

HRID 2372643Notes

Reaction equation

HRID 2372643 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15]C(OC)=O)=[CH:10][C:9]=1[N:20]1[C:24](=[O:25])[CH:23]([CH:26]([CH3:28])[CH3:27])[O:22][C:21]1=[O:29].[Cl-].[NH4+]>CO>[F:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([OH:15])=[CH:10][C:9]=1[N:20]1[C:24](=[O:25])[CH:23]([CH:26]([CH3:27])[CH3:28])[O:22][C:21]1=[O:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 14678341HCID 14678341, compound

Product 1

HCID 14678342HCID 14678342, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (3.04 g, 22.0 mmol) was added to a solution of 3-(2'-fluoro-4'-chloro-5'-methoxycarbonyloxyphenyl)-5-isopropyl-1,3-oxazolidine-2,4-dione (15.2 mg, 44.0 mmol) in dry methanol (150 ml) and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added and the product was extracted with ether. The ether layer was dried and the solvent was then distilled under reduced pressure to give a pale yellow oily product. The product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane×1/3) to give 3-(2'-fluoro-4'-chloro-5'-hydroxyphenyl)-5-isopropyl-1,3-oxazolidine-2,4-dione (10.5 g, yield 83%). The phenol derivative thus obtained (700 mg, 2.43 mmol) was dissolved in acetonitrile (30 ml). To the solution was added aryl bromide (2 ml) and potassium carbonate (340 mg) and the mixture was stirred for 3 hours under reflux. After completion of the reaction, the solvent was distilled under reduced pressure. After addition of 1N hydrochloric acid, the product was extracted with ether. The organic layer was dried and the solvent was distilled under reduced pressure to give a pale yellow oily product. The product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane×1/10) to give a pure product of 3-(2'-fluoro-4'-chloro-5'aryloxyphenyl)-5-isopropyl-1,3-oxazolidine-2,4-dione [Compound 7] (540 mg, yield 68%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe product was extracted with ether
  3. dry with materialThe ether layer was dried
  4. distillationthe solvent was then distilled under reduced pressure
  5. customto give a pale yellow oily product
  6. customThe product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane×1/3)

Sources & evidence

ORD record
ord-7b067fd519644ad79694372ff4bdecaa
Source dataset
uspto-grants-1992_03
Patent number
US05100457

Reaction notes

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