Potassium Hydroxide → 2,4-Dimethyl-5-carboxy-1H-pyrrole-3-propanoic acid 5-ethyl ester

HRID 24330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 24330
[CH3:1][C:2]1[NH:3][C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:5]([CH3:14])[C:6]=1[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10].[OH-].[K+]>O.CO>[CH2:18]([O:17][C:15]([C:4]1[NH:3][C:2]([CH3:1])=[C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[C:5]=1[CH3:14])=[O:16])[CH3:19]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 291761Ethyl 2,4-dimethyl-5-(ethoxycarbonyl)-3-pyrrolepropionate

Produkt 1

HCID 1422052,4-Dimethyl-5-carboxy-1H-pyrrole-3-propanoic acid 5-ethyl esterAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a suspension of 10 g (38.9 mmol) ethyl 2,4-dimethyl-5-(ethoxycarbonyl)-3-pyrrolepropionate (commercially available) in a mixture of water (250 mL) and methanol (MeOH) (50 mL) was added 3.0 g of KOH in 50 mL of water. The mixture was stirred at 70° C. for 4 hr. The reaction mixture was cooled and the methanol was stripped from the mixture under vacuum. The remaining solution was filtered and the filtrate was then acidified with 6N hydrochloric acid to pH 3. The precipitate which formed was collected by filtration, washed with a 2:1 mixture of water and ethanol and dried under vacuum to give 7.5 g of 4-(2-carboxy-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe remaining solution was filtered
  3. customThe precipitate which formed
  4. filtrationwas collected by filtration
  5. washwashed with a 2:1 mixture of water and ethanol
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b83993ba834544a5b266a7678a49131a
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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