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

HRID 397915ノート

反応式

HRID 397915 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 23925Iron触媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-0d4e59d30f634c5b9fc963f3fb5e1dee
出典データセット
uspto-grants-2003_08
特許番号
US06610723B2

反応ノート

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