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

HRID 1007506
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1007506
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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

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

Produkt 1

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

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-59ff1b95ad6f4c5a8d53ad9d8f698187
Quelldatensatz
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06794406B2

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