Sodium hydride → HCID 20131158, compound

HRID 845478Notes

Reaction equation

HRID 845478 reaction equation
[OH:1][CH:2]([CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[H-].[Na+].Br[CH2:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1>O1CCCC1>[N:4]1([CH2:3][CH:2]([O:1][CH2:19][C:20]2[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=2)[CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 20131152HCID 20131152, compound

Product 1

HCID 20131158HCID 20131158, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[2-hydroxy-3-(pentoxy)propyl]1H-imidazole (Example 29b, 2.12 g, 0.010 mol) in anhydrous tetrahydrofuran (15 ml) was treated with sodium hydride (0.44 g of a 60% dispersion in oil, 0.011 mol) and stirred at room temperature for 1 hour. Ethyl 4-(bromomethyl)benzoate (2.67 g, 0.011 mol) was then added and the mixture was stirred at room temperature for 12 hours. The solvent was evaporated off under reduced pressure and the residue was dissolved in ethyl acetate, washed with water and dried (MgSO4). The solvent was evaporated off under reduced pressure and the crude product was purified by column chromatography (silica gel, chloroform) to give ethyl 4-[[1-(1H-imidazol-1ylmethyl)-2-(pentoxy)ethoxy]methyl]benzoate as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. customThe solvent was evaporated off under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated off under reduced pressure
  7. customthe crude product was purified by column chromatography (silica gel, chloroform)

Sources & evidence

ORD record
ord-956e29cef0704b7e9680936b3046dfbd
Source dataset
uspto-grants-1988_07
Patent number
US04758573

Reaction notes

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