2,5-Dimethoxytetrahydrofuran → 2-Chloro-4-(1-pyrrolyl)benzoic acid methyl ester

HRID 1375383

Reaktionsgleichung

Reaktionsgleichung von HRID 1375383
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([Cl:12])[CH:3]=1.CO[CH:15]1[CH2:19][CH2:18][CH:17](OC)O1>C(O)(=O)C>[Cl:12][C:4]1[CH:3]=[C:2]([N:1]2[CH:15]=[CH:19][CH:18]=[CH:17]2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Komponenten

4

Edukt 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 11839197Methyl 4-Amino-2-chlorobenzoate

Produkt 1

HCID 47637352-Chloro-4-(1-pyrrolyl)benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

2.0 g of methyl 4-amino-2-chlorobenzoate were dissolved in 10 ml of acetic acid, 2.0 ml of 2,5-dimethoxytetrahydrofuran were added thereto, and the mixture was heated under reflux for 15 minutes. After cooling the reaction solution, the solvent was evaporated. The obtained residue was mixed with EtOAc and saturated NaHCO3 aq. and extracted. The organic layer was washed with brine, and dried over sodium sulfate anhydride. After evaporating the solvent, the residue was purified by silica gel column chromatography (hexane-EtOAc (4:1)) to obtain 2.1 g of methyl 2-chloro-4-(1H-pyrrol-1-yl)benzoate.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 minutes
  3. temperatureAfter cooling the reaction solution
  4. customthe solvent was evaporated
  5. additionThe obtained residue was mixed with EtOAc and saturated NaHCO3 aq.
  6. extractionextracted
  7. washThe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate anhydride
  9. customAfter evaporating the solvent
  10. customthe residue was purified by silica gel column chromatography (hexane-EtOAc (4:1))

Quellen und Nachweise

ORD-Eintrag
ord-0b9ce3db8d964bc38b3f860c55a53796
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169772B2

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