Acetic Acid → {1-[3-(1,1-Difluoro-ethyl)-phenyl]-1H-imidazol-4-yl}-methanol

HRID 1841241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1841241
[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([F:4])[CH3:3].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C([O:46][CH2:47][CH3:48])(OCC)OCC.[N+:49]([CH2:52]C(OCC)=O)([O-])=O.[C:58](O)(=O)C>[Fe]>[F:1][C:2]([C:5]1[CH:6]=[C:7]([N:8]2[CH:58]=[C:48]([CH2:47][OH:46])[N:49]=[CH:52]2)[CH:9]=[CH:10][CH:11]=1)([F:4])[CH3:3]

Komponenten

7

Edukt 5

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 180504Ceric ammonium nitrateHCID 234450923-(1,1-Difluoroethyl)aniline

Produkt 1

HCID 23445191{1-[3-(1,1-Difluoro-ethyl)-phenyl]-1H-imidazol-4-yl}-methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23925IronKatalysator

Versuchsvorschrift

Following the general method described in example 293, 3-(1,1-difluoro-ethyl)-aniline [R. O. Neri, J. G. Topliss, Ger. Offen. (1972), DE 2130452 19721221 CAN 78:124310]was reacted with triethyl orthoformate, ethyl nitroacetate and acetic acid followed by treatment with triethyl orthoformate, iron and acetic acid and subsequent alkaline hydrolysis. The isolated acid was directly reduced according to example 264, by reaction with BH3 THF complex followed by hydrolytic workup and the title compound was obtained as a white crystalline solid. Mp. 104-108° C. (H2O), MS: m/e=238 (M+).

Aufarbeitung

  1. customThe isolated acid was directly reduced according to example 264, by reaction with BH3 THF complex

Quellen und Nachweise

ORD-Eintrag
ord-2f176982b27c49df9e2e20cbd5e2f803
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06683097B2

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