5-Dimethylthiocarbamoyloxy-benzofuran-2-carboxylic acid methyl ester → Methyl 5-hydroxybenzofuran-2-carboxylate

HRID 984107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 984107
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14]C(=S)N(C)C)=[CH:10][C:8]=2[CH:9]=1)=[O:4]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:8]=2[CH:9]=1)=[O:4]

Komponenten

3

Edukt 1

HCID 207660095-Dimethylthiocarbamoyloxy-benzofuran-2-carboxylic acid methyl ester

Produkt 1

HCID 12208973Methyl 5-hydroxybenzofuran-2-carboxylateAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7583Diphenyl EtherLösungsmittel

Versuchsvorschrift

A solution of 5-dimethylthiocarbamoyloxy-benzofuran-2-carboxylic acid methyl ester (1.3 g, 4.7 mmol) in 25 mL diphenyl ether was heated at reflux for 2.5 hours. The reaction mixture was then cooled and the resulting precipitate collected. Purification by flash column chromatography (gradient elution: 100% hexanes to 45% EtOAc/hexanes), gave the title compound (0.58 g, 45%) as a brown solid.

Aufarbeitung

  1. temperatureat reflux for 2.5 hours
  2. temperatureThe reaction mixture was then cooled
  3. customthe resulting precipitate collected
  4. customPurification
  5. washby flash column chromatography (gradient elution: 100% hexanes to 45% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-066f150d61c14a148738f5535dffe990
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867224B2

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