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Ethyl Acetoacetate → 4-(4-(ethoxycarbonyl)-5-methyl-1H-pyrrol-3-yl)butanoic acid

HRID 661488
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 661488
Cl.[NH2:2][CH2:3][C:4](=O)[CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].[OH-].[Na+].[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=O.C([O-])([O-])=O.[Na+].[Na+]>P([O-])(O)(O)=O.[Na+].O>[CH2:21]([O:20][C:14]([C:15]1[C:4]([CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:3][NH:2][C:16]=1[CH3:18])=[O:19])[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8868Ethyl AcetoacetateHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 713866726-Amino-5-oxohexanoic acid hydrochloride

Produkt 1

HCID 593760204-(4-(ethoxycarbonyl)-5-methyl-1H-pyrrol-3-yl)butanoic acidAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 23672064Monosodium phosphateLösungsmittel2×

Versuchsvorschrift

6-amino-5-oxohexanoic acid hydrochloride (S1) 22.44 g (0.12 mol) (Lartillot, Serge. et al, Bulletin de la Societe Chimique de France, 1964, 4:783) was solved in about 6.1 L sodium dihydrogen phosphate buffer (300 g sodium dihydrogen phosphate was solved in 6 L water, then Saturated sodium hydroxide aqueous solution was added until a pH of about 6.5 was reached), and ethyl acetoacetate 16.12 g (0.12 mol) was added to the above-mentioned solution. The reaction solution was refluxed for half an hour, cooled to room temperature and Na2CO3 was added until a pH of about 8 was reached. The mixture was extracted with 100 ml CHCl3 and Aqueous phase was acidified with 6 mol/L HCl to pH 1. The brown solid was collected by filtration, washed with water and dried in vacuum condition to give 20.29 g (71%) 4-(4-(ethoxycarbonyl)-5-methyl-1H-pyrrol-3-yl)butanoic acid (S2).

Aufarbeitung

  1. additionwas added to the above-mentioned solution
  2. temperatureThe reaction solution was refluxed for half an hour
  3. extractionThe mixture was extracted with 100 ml CHCl3 and Aqueous phase
  4. filtrationThe brown solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuum condition

Quellen und Nachweise

ORD-Eintrag
ord-ab1722fc6e934c0da08fe8402505c25d
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08084621B2

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