(4-Methoxyphenyl)-2-thienylmethanone → 4-(Thiophene-2-carbonyl)phenol

HRID 1857126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1857126
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=1)=[O:7].C[S-].[Na+]>CN(C)C=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)=[O:7]

Komponenten

4

Edukt 2

HCID 77812(4-Methoxyphenyl)-2-thienylmethanoneHCID 4378561Sodium methanethiolate

Produkt 1

HCID 130205054-(Thiophene-2-carbonyl)phenolAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Methoxyphenyl 2-thienyl ketone (804 mg) obtained in Example 38 was dissolved in N,N-dimethylformamide (30 ml), sodium thiomethoxide (645 mg) was added, and the admixture was refluxed under argon for 5 hours. The reaction mixture was partitioned in the same manner as described in Example 33. The ethyl acetate layer was dried with anhydrous magnesium sulfate, the solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with chloroform to obtain 702 mg of the title compound (yield: 93%).

Aufarbeitung

  1. temperaturethe admixture was refluxed under argon for 5 hours
  2. customThe reaction mixture was partitioned in the same manner
  3. dry with materialThe ethyl acetate layer was dried with anhydrous magnesium sulfate
  4. customthe solvent was removed by reduced-pressure distillation
  5. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-27bc688160e54f4ab4619273933be1a4
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06143764

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