Sulfuric Acid → 4-(1-cis-Tridecenyl)pyrrole-2-carboxylic acid

HRID 1090748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090748
[OH-].[Na+].[CH:3](/[C:16]1[CH:17]=[C:18]([C:21]([O:23]C)=[O:22])[NH:19][CH:20]=1)=[CH:4]/[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].S(=O)(=O)(O)O>C(O)C>[CH:3](/[C:16]1[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[NH:19][CH:20]=1)=[CH:4]/[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 15023334Methyl 4-(1-cis tridecenyl)pyrrole-2-carboxylate

Produkt 1

HCID 150233324-(1-cis-Tridecenyl)pyrrole-2-carboxylic acidAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

An aqueous solution (25 ml) containing 860 mg (20.4 mmol) of 95% sodium hydroxide was added to an ethanol solution (50 ml) of 3.10 g (10.2 mmol) of methyl 4-(1-cis-tridecenyl)pyrrole-2-carboxylate prepared in Example 46, and the whole was heated under reflux for 1 hour. The reaction mixture was acidified with 6N sulfuric acid and extracted with ethyl acetate. The extract was washed with an aqueous saturated solution of sodium chloride, dried over anhydrous magnesium sulfate and treated with activated carbon. After removing the solvent under reduced pressure, the residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 1.33 g (45% yield) of 4-(1-cis-tridecenyl)pyrrole-2-carboxylic acid, m.p. 157°-158° C.

Aufarbeitung

  1. temperaturethe whole was heated
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additiontreated with activated carbon
  7. customAfter removing the solvent under reduced pressure
  8. customthe residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-369e85f070b44fa68104b5633ff918a5
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05082856

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