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Acetic Acid → 4-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethylphenylacetic acid

HRID 1007506
ノート
印刷プレビュー

反応式

HRID 1007506 の反応式
S(=O)(=O)(O)O.O.[CH:7]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][C:20]3[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][C:23](CC#N)=[CH:22][C:21]=3[C:33]([F:36])([F:35])[F:34])[CH:17]=2)[NH:12][CH:11]=1)([CH3:9])[CH3:8].C(OCC)(=O)C.[C:43]([OH:46])(=[O:45])[CH3:44]>>[CH:7]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][C:20]3[C:25]([C:26]([F:27])([F:29])[F:28])=[CH:24][C:23]([CH2:44][C:43]([OH:46])=[O:45])=[CH:22][C:21]=3[C:33]([F:36])([F:34])[F:35])[CH:17]=2)[NH:12][CH:11]=1)([CH3:9])[CH3:8]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 226696934-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-phenylacetonitrile

生成物 1

HCID 98035514-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethylphenylacetic acid

反応条件

温度
105 °C

実験手順

A mixture of 5 ml of concentrated sulphuric acid and 5 ml of water is added dropwise to a solution of 0.35 g (0.82 mmol) of nitrile derivative from Example VIII in 5 ml of acetic acid (100% strength). The reaction solution is stirred at 105° C. for 4 hours, then cooled to room temperature and treated with ice-cold water and ethyl acetate. The organic phase is separated off, the aqueous solution is extracted again with ethyl acetate, and the combined organic phases are dried over sodium sulphate, filtered and concentrated to give an oil. The crude product (120.3 mg) is chromatographed on silica gel 60 by means of methylene chloride/methanol (95:5 and95:11).

後処理

  1. temperaturecooled to room temperature
  2. customThe organic phase is separated off
  3. extractionthe aqueous solution is extracted again with ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe crude product (120.3 mg) is chromatographed on silica gel 60 by means of methylene chloride/methanol (95:5 and95:11)

出典と根拠

ORDレコード
ord-59ff1b95ad6f4c5a8d53ad9d8f698187
出典データセット
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06794406B2

反応ノート

読み込み中…

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