Sodium hydride → 8-[4-(2-Isopropoxyphenyl)imidazol-1-yl]octanoic acid methyl ester

HRID 1039175

Reaktionsgleichung

Reaktionsgleichung von HRID 1039175
[H-].[Na+].[CH:3]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:14]=[CH:15][NH:16][CH:17]=1)([CH3:5])[CH3:4].[CH3:18][O:19][C:20](=[O:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:18][O:19][C:20](=[O:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:16]1[CH:17]=[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH:3]([CH3:5])[CH3:4])[N:14]=[CH:15]1

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 11107373Methyl 8-bromooctanoateHCID 1784582854-[2-(propan-2-yloxy)phenyl]-1H-imidazole

Produkt 1

HCID 591678008-[4-(2-Isopropoxyphenyl)imidazol-1-yl]octanoic acid methyl esterAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Add sodium hydride (1.82 g, 38 mmol) to a suspension of 4-(2-isopropoxyphenyl)-1H-imidazole (5.01 g, 25 mmol) in THF (125 mL) at 0° C. under nitrogen, and warm the mixture to room temperature and stir for 1 hour. Cool the mixture to 0° C. and add 8-bromooctanoic acid methyl ester (5.98 g, 25 mmol) and tetra-n-butylammonium iodide (0.55 g, 1.5 mmol) and warm the mixture to room temperature to stir for 8 hours. Dilute the mixture with water (20 mL) and remove the solvent under reduced pressure. Dilute the residue with ethyl acetate (300 mL), wash with water (100 mL) and brine (100 mL), dry over sodium sulfate, and remove the solvent under reduced pressure to provide 8-[4-(2-isopropoxyphenyl)imidazol-1-yl]octanoic acid methyl ester (5.16 g, 57%), which is used in the next step without further purification.

Aufarbeitung

  1. temperatureCool the mixture to 0° C.
  2. temperaturewarm the mixture to room temperature
  3. stirringto stir for 8 hours
  4. customremove the solvent under reduced pressure
  5. additionDilute the residue with ethyl acetate (300 mL)
  6. washwash with water (100 mL) and brine (100 mL)
  7. dry with materialdry over sodium sulfate
  8. customremove the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e0df51e4888b4c41a02e544426edd101
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552039B2

Verknüpfte Notizen

Wird geladen…