Acetate → 4-(4-(2-Hydroxyphenyl)thiophenyl)butyric acid

HRID 19441

Reaktionsgleichung

Reaktionsgleichung von HRID 19441
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[SH:27].C([O-])(=O)C>CN(C)C=O>[OH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 175AcetateHCID 11430Potassium CarbonateHCID 70718Phenol, o-mercapto-(6CI,7CI,8CI)HCID 46454274-(p-Iodophenyl)butyric acid

Produkt 1

HCID 684943804-(4-(2-Hydroxyphenyl)thiophenyl)butyric acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(4-iodophenyl)butyric acid (0.86M) and dimethylformamide was treated with 2 eq of potassium carbonate, 1.5 eq of 2-hydroxythiophenol and a catalytic amount of cuperic acetate (0.01 eq). The reaction mixture was refluxed for 18 hr, cooled to 25 C, acidified with aqueous acid and extracted with ethyl acetate. The organic phase was concentrated. The residue was purified by flash chromatography using ethyl acetate/hexane as eluant to give 4-(4-(2-hydroxyphenyl)thiophenyl)butyric acid.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 18 hr
  2. temperaturecooled to 25 C
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase was concentrated
  5. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e7e01cb1d6b341e290203e4523dd3350
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07744910B2

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