Water → HCID 15895912, compound

HRID 1871476Notes

Reaction equation

HRID 1871476 reaction equation
[CH3:1][C:2]1[N:3]([CH2:7][CH2:8][C:9]([O:11]CC)=O)[CH:4]=[CH:5][N:6]=1.[C:14]1([Li])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>O1CCCC1>[CH3:1][C:2]1[N:3]([CH2:7][CH2:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[OH:11])[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2764366ethyl 3-(2-methyl-1H-imidazol-1-yl)propanoateHCID 178506676HCID 178506676, compound

Product 1

HCID 15895912HCID 15895912, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

In a 200 ml two-neck flask, under an atmosphere of argon, a solution of ethyl 3-(2-methyl-1-imidazolyl)propionate (3.37 g, 18.5 mmol) in anhydrous tetrahydrofuran was added to 50 ml of 1.8M phenyllithium solution at 0° C. After stirred for 3.5 hours at 10° C., the mixture was allowed to stand overnight at room temperature. The solution was poured into water, which was extracted with ethyl acetate. The organic extract was washed with saturated saline solution and dried over anhydrous sodium sulfate, followed by concentration. The residue was purified by silica gel chromatography (elution solvent; ethyl acetate-ethanol=10:1) and then recrystallized from n-hexane-ethyl acetate. This was further recrystallized from ethanol-benzene to give 320 mg of title compound as white needle-like crystals. Yield: 6%

Workup

  1. waitto stand overnight at room temperature
  2. extractionwas extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationfollowed by concentration
  7. customThe residue was purified by silica gel chromatography (elution solvent; ethyl acetate-ethanol=10:1)
  8. customrecrystallized from n-hexane-ethyl acetate
  9. customThis was further recrystallized from ethanol-benzene

Sources & evidence

ORD record
ord-f4630a1fdb774b95a82b6e1ea3563990
Source dataset
uspto-grants-2000_08
Patent number
US06103747

Reaction notes

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