Sodium hydride → HCID 86747877, compound

HRID 1033909Notes

Reaction equation

HRID 1033909 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[N:8]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:9](/[CH:12]=[C:13](\CC2C=CC=CC=2)/[CH2:14][OH:15])=[CH:10][N:11]=1)[CH2:4][CH2:5][CH3:6].Br[CH2:32][C:33]([O:35]C)=[O:34]>C(COC)OC>[CH2:3]([C:7]1[N:8]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:9]([CH2:12]/[CH:13]=[CH:14]/[O:15][CH:32]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:33]([OH:35])=[O:34])=[CH:10][N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 67849156HCID 67849156, compound

Product 1

HCID 86747877HCID 86747877, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of sodium hydride (2.3 mml)in 5 mL of glyme is added portionwise (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-benzyl-2-propenol prepared by the method of Example 18(i) from the methyl ester of the compound of Example 2. After stirring for 30 minutes, methyl bromoacetate (2.2 mmol) is added dropwise The reaction is stirred overnight at room temperature and then the mixture is poured into ice/water. The product is extracted into ethyl acetate (3×). The combined organic extracts are washed with water and brine and dried with anhydrous magnesium sulfate. The solvent is removed in vacuo. The residue is chromatographed on silica gel to give the esters of the title compound as an oil.

Workup

  1. stirringis stirred overnight at room temperature
  2. extractionThe product is extracted into ethyl acetate (3×)
  3. washThe combined organic extracts are washed with water and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent is removed in vacuo
  6. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-f47e68406ee443c993461516e1afae5b
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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