Water → 4-Ethoxycarbonyl-2-fluoro-1-triphenylmethylimidazole

HRID 1463166Notes

Reaction equation

HRID 1463166 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([F:28])[N:7]([C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=1)([OH:3])=[O:2].[CH2:29](I)[CH3:30].O>C1COCC1>[CH2:29]([O:2][C:1]([C:4]1[N:5]=[C:6]([F:28])[N:7]([C:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:8]=1)=[O:3])[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 6340IodoethaneHCID 204324044-Carboxy-2-fluoro-1-triphenylmethylimidazole

Product 1

HCID 204519154-Ethoxycarbonyl-2-fluoro-1-triphenylmethylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-carboxy-2-fluoro-1-triphenylmethylimidazole (280 mg.) in THF (0.75 ml.) was treated, under argon with 1,5-diazabicyclo-5,4,0-undec-5-ene (0.112 ml.) followed by ethyl iodide (0.069 ml.). The mixture was stirred for two hours at room temperature, water was added and the mixture extracted, with ether. The ether extract was dried (MgSO4) and evaporated to give 4-ethoxycarbonyl-2-fluoro-1-triphenylmethylimidazole (185 mg.) as a yellow foam having the following n.m.r. in CDCl3 : 1.38 (t, 3H); 4.36 (q, 2H); 7.0-7.5 (m, 16H).

Workup

  1. extractionthe mixture extracted, with ether
  2. extractionThe ether extract
  3. dry with materialwas dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-f8df1be1f15342b180c054a609d5532d
Source dataset
uspto-grants-1984_07
Patent number
US04463173

Reaction notes

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