Imidazole → HCID 57815679, compound

HRID 1664072Notes

Reaction equation

HRID 1664072 reaction equation
[H-].[Na+].[CH2:3]([O:13][CH2:14][CH2:15][CH2:16][CH2:17]Br)/[CH:4]=[C:5](/[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])\[CH3:6].[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>>[CH2:3]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)/[CH:4]=[C:5](/[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])\[CH3:6]

Participants

4

Reactant 3

HCID 795Imidazole2×HCID 24758Sodium hydrideHCID 57815681HCID 57815681, compound

Product 1

HCID 57815679HCID 57815679, compoundYield 90.6%

Procedure

Sodium hydride (1.1 g 60% dispersion in oil, 0.66 g, 27.5 mmol) was weighed out in a 100 mL round bottom flask. The sodium hydride was washed with hexane (3×5 mL) to remove the mineral oils. DMF (anhydrous, 20 mL) was added, followed by geranyloxybutyl bromide (1.51 g, 5.47 mmol). The reaction mixture was stirred at room temperature under N2 for a couple of minutes. Imidazole (1.84 g, 103 mmol, 27.1 equiv) was added slowly in small portions while cooling in an ice bath. The addition of imidazole was exothermic and the reaction mixture bubbled vigorously becoming initially a milky off-white and then clear brown in colour. This was left stirring at room temperature overnight. The reaction mixture was diluted with chloroform (50 mL) and then it was washed with brine (3×50 mL), and dried (Na2SO4). The solvent was removed under reduced pressure followed by high vacuum to give the product as a brown oil (1.37 g, 90%).

Workup

  1. washThe sodium hydride was washed with hexane (3×5 mL)
  2. customto remove the mineral oils
  3. additionDMF (anhydrous, 20 mL) was added
  4. temperaturewhile cooling in an ice bath
  5. customthe reaction mixture bubbled vigorously
  6. waitThis was left
  7. stirringstirring at room temperature overnight
  8. additionThe reaction mixture was diluted with chloroform (50 mL)
  9. washit was washed with brine (3×50 mL)
  10. dry with materialdried (Na2SO4)
  11. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b2a801d9a83643a68e1b4a918e5d6127
Source dataset
uspto-grants-2011_10
Patent number
US08038737B2

Reaction notes

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