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Glycine → Methyl (1H-pyrrol-1-yl)acetate

HRID 1742016
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1742016
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[C:6]([O-])(=O)C.[K+].CO[CH:13]1[CH2:17][CH2:16][CH:15](OC)O1.C(=O)(O)[O-].[Na+]>O.C(O)(=O)C>[N:1]1([CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH:13]=[CH:17][CH:16]=[CH:15]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 750GlycineHCID 790982,5-DimethoxytetrahydrofuranHCID 516892Sodium BicarbonateHCID 517044Potassium Acetate

Produkt 1

HCID 11217296Methyl (1H-pyrrol-1-yl)acetateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of the hydrochloride salt of the methyl ester of glycine (6.30 g) and potassium acetate (8.00 g) in water (10 ml) was added to glacial acetic acid (50 ml). The resulting mixture was heated to reflux, 2,5-dimethoxytetrahydrofuran (6.60 g) was added in one portion, and heating under reflux was continued for 4 hours. After cooling, the reaction mixture was neutralised with sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, dried, concentrated under reduced pressure, and distilled at 125° C. and ca. 15 torr using a short-path distillation apparatus to give methyl pyrrol-1-ylacetate (2.62 g, 38% yield) as a colourless liquid, infra red (film) 1750 cm-1.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. temperatureheating
  4. temperatureunder reflux
  5. temperatureAfter cooling
  6. extractionextracted with ethyl acetate
  7. washThe extracts were washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. distillationdistilled at 125° C.

Quellen und Nachweise

ORD-Eintrag
ord-06ebf1c6cd1c4e759e68eceed0f73e39
Quelldatensatz
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05336682

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