Ethyl Acetate → Methyl 3-methylsulfonyl-5-(pyrrol-1-yl)benzoate

HRID 399791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 399791
[NH2:1][C:2]1[CH:3]=[C:4]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[CH3:15][S:12]([C:4]1[CH:5]=[C:6]([CH:11]=[C:2]([N:1]2[CH:18]=[CH:22][CH:21]=[CH:20]2)[CH:3]=1)[C:7]([O:9][CH3:10])=[O:8])(=[O:14])=[O:13]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 790982,5-DimethoxytetrahydrofuranHCID 18945412Methyl 3-amino-5-(methylsulfonyl)benzoate

Produkt 1

HCID 18945432Methyl 3-methylsulfonyl-5-(pyrrol-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

The mixture of methyl 5-amino-3-methylsulfonylbenzoate (1.5 g) and 2,5-dimethoxytetrahydrofuran (1.3 ml) in acetic acid (4.5 ml) was heated under reflux for 2 hours under stirring. After cooling, the mixture was poured into a mixture of ethyl acetate and water, and adjusted to pH 8 with 20% aqueous potassium carbonate solution. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and the residue was triturated with diisopropyl ether to give methyl 3-methylsulfonyl-5-(pyrrol-1-yl)benzoate (1.58 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed by concentration
  7. customthe residue was triturated with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-43600cd00ec94bc1aedc71ed6ce3b30a
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05824691

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