Water → HCID 22259332, compound

HRID 1610947Notes

Reaction equation

HRID 1610947 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:8][CH2:9][OH:10].[C:11]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25]I)=[CH:18][CH:17]=1)([CH3:14])([CH3:13])[CH3:12].O>CN(C=O)C>[C:11]([O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][N:3]2[CH:7]=[CH:6][N:5]=[C:4]2[CH2:8][CH2:9][OH:10])=[CH:20][CH:21]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12992838HCID 12992838, compoundHCID 150160802-(1H-imidazol-2-yl)ethan-1-ol

Product 1

HCID 22259332HCID 22259332, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

65% sodium hydride (1.78 g) was added to a solution of 2-(1H-imidazol-2-yl)ethanol (5.62 g) in DMF (80 ml) at 0° C., and the mixture was stirred at room temperature for 30 min. A solution of 1-tert-butoxy-4-(4-iodobutyl)benzene (13.3 g) in DMF (20 ml) was added to the mixture at 0° C., and the mixture was stirred at the same temperature for 5 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was washed successively with water (twice), and saturated brine, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Chromatorex; eluent hexane:ethyl acetate=2:5) to give the titled compound (9.53 g) as a colorless amorphous form.

Workup

  1. stirringthe mixture was stirred at the same temperature for 5 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with water (twice), and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (Chromatorex; eluent hexane:ethyl acetate=2:5)

Sources & evidence

ORD record
ord-1a76d7bd083f4e958a65a062e56c967f
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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