Acetic Acid → 2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbaldehyde

HRID 1661946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1661946
[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[C:9]([O:15][CH3:16])=[CH:10]C(C#N)=[CH:12][C:7]=2[N:6]=[C:5]1[C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=1.[C:26]([OH:29])(=O)[CH3:27].[PH2]([O-])=O.[Na+].N1C=CC=C[CH:35]=1>O.[Ni]>[CH:23]([C:20]1[CH:21]=[CH:22][C:17]([C:5]2[N:4]([CH2:3][CH2:2][O:1][CH3:35])[C:8]3[C:9]([O:15][CH3:16])=[CH:10][C:27]([CH:26]=[O:29])=[CH:12][C:7]=3[N:6]=2)=[CH:18][CH:19]=1)([CH3:25])[CH3:24]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 1049PyridineHCID 674309111-(2-Hydroxy-ethyl)-2-(4-isopropyl-phenyl)-7-methoxy-1H-benzoimidazole-5-carbonitrileHCID 178527019HCID 178527019, Verbindung

Produkt 1

HCID 577720462-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 7.02 g (20.1 mmol) of 1-(2-Hydroxy-ethyl)-2-(4-isopropyl-phenyl)-7-methoxy-1H-benzoimidazole-5-carbonitrile in 280 ml pyridine is added 140 ml acetic acid. After addition of a solution of 14.1 g (161 mmol) sodium hypophosphite in 140 ml water and heating to 50° C. Raney-Nickel is added in 50 mg portions (3× over 12 h) until the reaction is complete. The reaction mixtures is cooled to RT, ice/water is added and the reaction mixture is extracted with ethyl acetate (3×). The organic layer is washed with water, in vacuo and azeotroped with toluene. The residue is suspended in 100 ml CH2Cl2, filtered and washed with CH2Cl2 and ethyl acetate. The mother liquor is evaporated and purified by flash-chromatography on silica gel (hexanes/EtOAc) to give 3.78 g of colorless crystals.

Aufarbeitung

  1. customThe reaction mixtures
  2. temperatureis cooled to RT
  3. extractionthe reaction mixture is extracted with ethyl acetate (3×)
  4. washThe organic layer is washed with water, in vacuo
  5. customazeotroped with toluene
  6. filtrationfiltered
  7. washwashed with CH2Cl2 and ethyl acetate
  8. customThe mother liquor is evaporated
  9. custompurified by flash-chromatography on silica gel (hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-77fcf9c3ea4b4a4080167a39e99f0b9a
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030497B2

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