Hexane → HCID 17962977, compound

HRID 1983811Notes

Reaction equation

HRID 1983811 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.C([Li])CCC.CCCCCC.[CH3:24][C:25](=[C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28]1)[CH3:26].[Cl-].[NH4+]>O1CCCC1>[CH2:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27]([C:25]([CH3:26])([CH3:24])[CH2:1][C:2]2[N:3]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:4]=[CH:5][N:6]=2)=[CH:28]1

Participants

7

Reactant 5

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 1186931-(1-Methylethylidene)-1H-indeneHCID 12277631HCID 12277631, compoundHCID 178418339Butyllithium

Product 1

HCID 17962977HCID 17962977, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 1.58 g 2-methyl-1-phenyl-1H-imidazole (10 mmol) in 15 ml of tetrahydrofuran was cooled to −78° C. and 6.25 ml of 15% n-butyl-lithium in hexane (10 mmol) were added. The resulting mixture was stirred for an additional 20 min and then treated with a solution of 1.56 g 1-(1-methylethylidene)-1H-indene (10 mmol) in 5 ml tetrahydrofuran with vigorous stirring while the temperature was maintained at −78° C. The reaction mixture was allowed to reach room temperature, stirred for 14 h and hydrolyzed with saturated ammonium chloride solution. The organic layer was isolated and the aqueous layer was extracted three times with dichloromethane. The organic layers were dried over MgSO4, filtered and the solvent removed. The crude product was purified by column chromatography with silica as stationary phase. At the beginning a 5/1 hexane/ethyl acetate elution mixture was used (for the separation from 1-(1-methylethylidene)-1H-indene). Then, the elution mixture was changed to 1/1 hexane/ethyl acetate. After removal of the solvent 2.13 g (69%) of 2-[2-(1H-inden-3-yl)-2-methylpropyl]-1-phenyl-1H-imidazole was obtained as an oil.

Workup

  1. stirringwith vigorous stirring while the temperature
  2. customto reach room temperature
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer was extracted three times with dichloromethane
  5. dry with materialThe organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed
  8. customThe crude product was purified by column chromatography with silica as stationary phase
  9. washAt the beginning a 5/1 hexane/ethyl acetate elution mixture
  10. customfor the separation from 1-(1-methylethylidene)-1H-indene)
  11. customAfter removal of the solvent 2.13 g (69%) of 2-[2-(1H-inden-3-yl)-2-methylpropyl]-1-phenyl-1H-imidazole
  12. customwas obtained as an oil

Sources & evidence

ORD record
ord-71b743ce58e744bbbcce1f4ce19c2a09
Source dataset
uspto-grants-2009_06
Patent number
US07541481B2

Reaction notes

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