Cuminol → Imidazole-1-carboxylic acid-(4-isopropyl)benzyl ester

HRID 1269510

Reaktionsgleichung

Reaktionsgleichung von HRID 1269510
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:12](N1C=CN=C1)([N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[O:13]>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:12]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[O:13])=[CH:10][CH:11]=1)([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 325CuminolHCID 682631,1'-Carbonyldiimidazole

Produkt 1

HCID 18448505Imidazole-1-carboxylic acid-(4-isopropyl)benzyl esterAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-isopropylbenzyl alcohol (4.51 g, 30.02 mmol) in 50 mL toluene was added 1,1′-carbonyldiimidazole (4.87 g, 30.02 mmol). This solution was stirred 18 h at ambient temperature. White precipitate was filtered off and the filtrate was concentrated under reduced pressure. The resultant oil was flash chromatographed with 15% ethyl acetate/hexanes to yield 6.41 g (87%) of imidazole-1-carboxylic acid-(4-isopropyl)benzyl ester, a clear oil.

Aufarbeitung

  1. filtrationWhite precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customchromatographed with 15% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1685956851ef457384e661d9331fbdf2
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199243B2

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