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

HRID 433611Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 433611
[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-6d9e6d62dee541cab4a74d9691eb3017
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06667335B2

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