Water → 2,2-Dimethyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propyl acetate

HRID 432567Notes

Reaction equation

HRID 432567 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:2]=1.[OH-].[K+].[C:14]([O:17][CH2:18][C:19]([CH3:23])([CH3:22])[CH2:20]Br)(=[O:16])[CH3:15].O>CS(C)=O.C(Cl)(Cl)Cl>[C:14]([O:17][CH2:18][C:19]([CH3:23])([CH3:22])[CH2:20][N:10]1[CH:11]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[N:8]=[CH:9]1)(=[O:16])[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 133577153-Bromo-2,2-dimethylpropyl acetateHCID 178420772HCID 178420772, compound

Product 1

HCID 545188152,2-Dimethyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propyl acetate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-pyridin-3-yl-imidazole (50 mg) in DMSO (methyl sulfoxide) (1.7 mL) was added powered KOH (57 mg) and 3-bromo-2,2-dimethylpropyl acetate and the resulting suspension was heated at 70° C. for 48 hours. Water was added followed by CHCl3, the aqueous layer was extracted with CHCl3, the combined organic layers were washed with brine, dired over Na2SO4 and evaporated in vacuo. The redisue was purified by preparative TLC (10% MeOH-90% CH2Cl2) the title compound as slightly yellow oil.

Workup

  1. extractionthe aqueous layer was extracted with CHCl3
  2. washthe combined organic layers were washed with brine
  3. customevaporated in vacuo
  4. customThe redisue was purified by preparative TLC (10% MeOH-90% CH2Cl2) the title compound as slightly yellow oil

Sources & evidence

ORD record
ord-2040a0ba66db4bc4aaea4c1bbbd3f2db
Source dataset
uspto-grants-2003_12
Patent number
US06664238B1

Reaction notes

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