Water → 5-[2-(p-[Ethoxycarbonylmethoxy]phenyl)ethen-1-yl]imidazo[1,5-a]pyridine

HRID 280228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280228
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].O>CN(C)C=O>[CH2:26]([O:25][C:23]([CH2:22][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1)=[O:24])[CH3:27]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 540585275-[2-(p-Hydroxyphenyl)ethen-1-yl]imidazo[1,5-a]pyridine

Produkt 1

HCID 538749585-[2-(p-[Ethoxycarbonylmethoxy]phenyl)ethen-1-yl]imidazo[1,5-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 5-[2-(p-hydroxyphenyl)ethen-1-yl]imidazo[1,5-a]pyridine (2.36 g) in 10 ml of dimethylformamide is added to a slurry of 0.5 g of sodium hydride in 30 ml of dry dimethylformamide at 0° under nitrogen. After warming to room temperature ethyl bromoacetate (1.67 g) is added and the reaction is heated to 60° for 5 hours. Water (200 ml) is added and the solution is extracted with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulfate and evaporated to yield 5-[2-(p-[ethoxycarbonylmethoxy]phenyl)ethen-1-yl]imidazo[1,5-a]pyridine.

Aufarbeitung

  1. additionis added
  2. temperaturethe reaction is heated to 60° for 5 hours
  3. extractionthe solution is extracted with ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c6101cfb69cd4263aba46af87fd668f3
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588732

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