Benzil → 3-(4,5-diphenyl-1H-imidazol-2-yl)propionic acid methyl ester

HRID 220261

Reaktionsgleichung

Reaktionsgleichung von HRID 220261
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][CH:19]([O:26]C)[CH2:20][CH2:21][C:22](OC)=O.C([O-])(=O)C.[NH4+:32].[OH-].[NH4+:34]>C(O)(=O)C.O>[CH3:17][O:18][C:19](=[O:26])[CH2:20][CH2:21][C:22]1[NH:32][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:34]=1

Komponenten

7

Edukt 4

HCID 8651BenzilHCID 14923Ammonium HydroxideHCID 350846Methyl 4,4-dimethoxybutanoateHCID 517165Ammonium Acetate

Produkt 1

HCID 684138073-(4,5-diphenyl-1H-imidazol-2-yl)propionic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 1 g of benzil, 1.01 g of methyl 4,4-dimethoxybutyrate and 2.87 g of ammonium acetate in 23 mL of acetic acid was refluxed for 5 h. The mixture was poured into water, basified with a 25% aq. ammonium hydroxide solution and extracted with DCM. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using heptane/EtOAc from 85/15 to 0/100 as eluant to yield 633 mg of 3-(4,5-diphenyl-1H-imidazol-2-yl)-propionic acid methyl ester as a yellowish solid.

Aufarbeitung

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over anh. Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude material was purified by CC

Quellen und Nachweise

ORD-Eintrag
ord-892bcec21f6c40609c2057332dd0077b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202885B2

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