Potassium Carbonate → HCID 67338116, Verbindung

HRID 1670141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670141
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2].[Br:30][C:31]1[CH:32]=[C:33]([CH:39]=[C:40]([OH:42])[CH:41]=1)[C:34]([N:36]([CH3:38])[CH3:37])=[O:35].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CC(C)=O.O.Cl>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:42][C:40]2[CH:39]=[C:33]([C:34](=[O:35])[N:36]([CH3:38])[CH3:37])[CH:32]=[C:31]([Br:30])[CH:41]=2)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2]

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterHCID 57905868HCID 57905868, Verbindung

Produkt 1

HCID 67338116HCID 67338116, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 180AcetoneLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (3.48 g, 7.4 mmol), 3-bromo-5-hydroxy-N,N-dimethyl-benzamide (1.5 g, 6.17 mmol) in N,N-dimethylformamide (30 mL) and acetone (60 mL) was added potassium carbonate (8.51 g, 61.7 mmol). The resulting suspension was heated to 70° C. for 24 h. Then the reaction mixture was cooled to room temperature and diluted with water and 10% aq. HCl. The organic compound was extracted into ethyl acetate and the combined organic extracts were washed with water and brine solution. The organic extracts were dried over anhydrous sodium sulfate and removal of the solvent under reduced pressure gave the crude product which was purified on ISCO™ column (120 g) using 50% ethyl acetate in hexanes as eluting solvent to give the title compound (3.1 g, 80%) as colorless oil.

Aufarbeitung

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. extractionThe organic compound was extracted into ethyl acetate
  3. washthe combined organic extracts were washed with water and brine solution
  4. dry with materialThe organic extracts were dried over anhydrous sodium sulfate and removal of the solvent under reduced pressure
  5. customgave the crude product which
  6. customwas purified on ISCO™ column (120 g)
  7. washas eluting solvent

Quellen und Nachweise

ORD-Eintrag
ord-d6fc8f419e1846ecbd368af6db791cb1
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989454B2

Notizen zur Reaktion

Wird geladen…