Hydrochloric Acid → 3-Hydroxy-2-(p-methoxyphenyl)-5-trifluoromethylbenzo[b]thiophene

HRID 978085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 978085
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:26]=[CH:25][C:8]([CH2:9][S:10][C:11]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:12]=2[C:13]([O:15]C)=O)=[CH:7][CH:6]=1.O.Cl>CN(C)C=O>[OH:15][C:13]1[C:12]2[CH:17]=[C:18]([C:21]([F:22])([F:24])[F:23])[CH:19]=[CH:20][C:11]=2[S:10][C:9]=1[C:8]1[CH:25]=[CH:26][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24758Sodium hydrideHCID 20205034Methyl 2-(p-methoxybenzylthio)-5-trifluoromethylbenzoate

Produkt 1

HCID 202050203-Hydroxy-2-(p-methoxyphenyl)-5-trifluoromethylbenzo[b]thiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a mixture of sodium hydride (50% dispersion in mineral oil) (134 mg, 2.79 mmol) in N,N-dimethylformamide (3 ml) at 75° C. under a nitrogen atmosphere was added dropwise with stirring a solution of methyl 2-(p-methoxybenzylthio)-5-trifluoromethylbenzoate (500 mg, 1.40 mmol) in N,N-dimethylformamide (10 ml). After stirring 30 minutes at 75° C., the mixture was poured into water (50 ml), the mixture brought to pH5 with 2N hydrochloric acid, the product extracted with diethyl ether, the combined extracts washed with water, dried (sodium sulfate), and evaporated. The residue was chromatographed on a column of silica gel (Merck 7734, packed as a slurry in 25:1 hexane-ether). Elution with 25:1 hexane-ether containing 1% acetic acid afforded the desired product as a white solid upon evaporation of the appropriate fractions; yield 385 mg (85%); m/z 324 (M+.).

Aufarbeitung

  1. additionwas added dropwise
  2. extractionthe product extracted with diethyl ether
  3. washthe combined extracts washed with water
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customThe residue was chromatographed on a column of silica gel (Merck 7734
  7. washElution with 25:1 hexane-ether containing 1% acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-3feef361eedd4a3a9a00a5a6d88a2783
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04663344

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