Potassium Carbonate → HCID 14678342、化合物

HRID 2372643ノート

反応式

HRID 2372643 の反応式
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]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 14678341HCID 14678341、化合物

生成物 1

HCID 14678342HCID 14678342、化合物収率 83%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-7b067fd519644ad79694372ff4bdecaa
出典データセット
uspto-grants-1992_03
特許番号
US05100457

反応ノート

読み込み中…