Water → 2-(3-formyl-1H-indol-1-yl)acetic acid

HRID 1361000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361000
C([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]=[O:16])=[CH:7]1)C.[OH-].[Na+].O>O1CCOCC1>[CH:15]([C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]([CH2:5][C:4]([OH:17])=[O:3])[CH:7]=1)=[O:16]

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 801676(3-Formyl-indol-1-yl)-acetic acid ethyl ester

Produkt 1

HCID 7714652-(3-formyl-1H-indol-1-yl)acetic acidAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(3-Formylindol-1-yl)acetic acid ethyl ester (15.9 g 69 mmol) was dissolved in 1,4-dioxane (100 mL) and 1N sodium hydroxide (10 mL) was added and the resulting mixture was stirred at room temperature for 4 days. Water (500 mL) was added and the mixture was washed with diethyl ether (150 mL). The aqueous phase was acidified with 5N hydrochloric acid and extracted with ethyl acetate (250+150 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to afford 10.3 g (73%) of (3-formylindol-1-yl)acetic acid as a solid.

Aufarbeitung

  1. washthe mixture was washed with diethyl ether (150 mL)
  2. extractionextracted with ethyl acetate (250+150 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6e3a2e66e4d749c9bc3d313ef6530b0c
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879893B2

Notizen zur Reaktion

Wird geladen…