Potassium Hydroxide → E-1-cinnamyl-2-fluoro-imidazole

HRID 2412515Notes

Reaction equation

HRID 2412515 reaction equation
Cl.[F:2][C:3]1[NH:4][CH:5]=[CH:6][N:7]=1.[OH-].[K+].[CH2:10](Br)/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(C)=O>[CH2:10]([N:4]1[CH:5]=[CH:6][N:7]=[C:3]1[F:2])/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 5357478Cinnamyl bromideHCID 126246272-Fluoro-1H-imidazole hydrochloride

Product 1

HCID 20432440E-1-cinnamyl-2-fluoro-imidazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Fluoroimidazole hydrochloride was added to a suspension of powdered KOH in acetone, stirred for 10 minutes, and E-cinnamyl bromide added. After stirring 1 hour, the mixture was worked up by extraction and chromatography to give E-1-cinnamyl-2-fluoro-imidazole, having the following n.m.r. in CDCl3 : 4.6 (d, 2H); 6.1-6.4 (d of t, 1H); 6.6 (d, 1H); 6.6-6.8 (m, 2H); 7.2-7.5 (m, 5H).

Workup

  1. stirringAfter stirring 1 hour
  2. extractionthe mixture was worked up by extraction and chromatography

Sources & evidence

ORD record
ord-bca4cc9ebde1448ab07a897cc66b562a
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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