Dimethylformamide → Ethyl 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]acetate

HRID 1754371Notes

Reaction equation

HRID 1754371 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH:11]=[CH2:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].[CH3:24][CH2:25][O:26][C:27]([CH2:29]Br)=[O:28]>O.C1COCC1>[CH3:1][C:2]1[N:3]([CH2:29][C:27]([O:26][CH2:25][CH3:24])=[O:28])[C:4]([CH:11]=[CH2:12])=[C:5]([C:7]([F:10])([F:8])[F:9])[N:6]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178437817HCID 178437817, compound

Product 1

HCID 86724376Ethyl 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]acetateYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methyl-4-(trifluoromethyl)-5-vinyl-1H-imidazole (911 mg, 5.17 mmol) was added DMF (7 mL) and THF (3 mL), followed by K2CO3 (1.43 g, 10.35 mmol) and ethyl bromo acetate (687 mL, 6.2 mmol). The resulting mixture was then stirred overnight at room temperature. Water (50 mL) was added and the mixture was extracted with EtOAc (3×100 mL). The combined EtOAc layers were dried (MgSO4), concentrated in vacuo, and purified by flash chromatography (SiO2, 60% EtOAc/hexanes) to obtain the desired ethyl 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]acetate (796 mg, 3.03 mmol, 59% yield) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×100 mL)
  2. dry with materialThe combined EtOAc layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (SiO2, 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-da94efa4d6144e62ba5bdb2c0534b0de
Source dataset
uspto-grants-2015_10
Patent number
US09169248B2

Reaction notes

Loading…