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Sodium Hydroxide → 3-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butan-1-ol

HRID 844574
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 844574
CC1C=C(C=C(C)C=1)C([O:7][CH2:8][CH2:9][CH:10]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=1)[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[C:17](=[O:26])[C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=1)=O.[OH-].[Na+]>CO>[Cl:34][C:29]1[CH:28]=[C:27]([CH:10]([CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:17](=[O:26])[C:18]2[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=2)[CH2:9][CH2:8][OH:7])[CH:32]=[CH:31][C:30]=1[Cl:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 226138023-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butyl 3,5-dimethylbenzoate

Produkt 1

HCID 226138373-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butan-1-olAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

3-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butyl 3,5-dimethylbenzoate (0.93 g) (see Preparation 31) was dissolved in methanol (10 ml) and 2N aqueous sodium hydroxide solution (2 ml) added. A thick gum formed, additional methanol was added (50 ml) and the resulting suspension stirred at room temperature overnight. The methanol was then removed under reduced pressure and the residue partitioned between dichloromethane (50 ml) and water (10 ml). The organic phase was separated, washed with brine and the solvent removed under reduced pressure to give the crude product which was chromatographed on silica gel eluting with a solvent gradient of 99:1 changing to 95:5, by volume, dichloromethane:methanol, to give 3-(3,4-dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butan-1-ol (0.67 g) as a white foam.

Aufarbeitung

  1. customA thick gum formed
  2. customThe methanol was then removed under reduced pressure
  3. customthe residue partitioned between dichloromethane (50 ml) and water (10 ml)
  4. customThe organic phase was separated
  5. washwashed with brine
  6. customthe solvent removed under reduced pressure
  7. customto give the crude product which
  8. customwas chromatographed on silica gel eluting with a solvent gradient of 99:1 changing to 95:5, by volume, dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-84fa19497dfd47cd83d8b84bea880ee1
Quelldatensatz
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06380396B1

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