Tetrabutylammonium Fluoride → 3-[2-[1-(1-ethoxyethyl)-4,5-diphenyl-1H-imidazol-2-yl]ethyl]-phenol

HRID 1085816Notes

Reaction equation

HRID 1085816 reaction equation
C([Li])CCC.[CH2:6]([O:8][CH:9]([N:11]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:13]=[C:12]1[CH3:28])[CH3:10])[CH3:7].Br[CH2:30][C:31]1[CH:32]=[C:33]([CH:42]=[CH:43][CH:44]=1)[O:34][Si](C)(C)C(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCCCCC.C1COCC1>[CH2:6]([O:8][CH:9]([N:11]1[C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:13]=[C:12]1[CH2:28][CH2:30][C:31]1[CH:32]=[C:33]([OH:34])[CH:42]=[CH:43][CH:44]=1)[CH3:10])[CH3:7]

Participants

7

Reactant 4

HCID 2724141Tetrabutylammonium FluorideHCID 10040514[3-(Bromomethyl)phenoxy](tert-butyl)dimethylsilaneHCID 103804501-(1-ethoxyethyl)-2-methyl-4,5-diphenyl-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 104318323-[2-[1-(1-ethoxyethyl)-4,5-diphenyl-1H-imidazol-2-yl]ethyl]-phenolYield 39%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (3.89 g, 61mmol) in hexane (24.31 mL) was added dropwise to a stirred solution of 1-(1-ethoxyethyl)-2-methyl-4,5-diphenyl-1H-imidazole (l5.50 g, 51 mmol) in dry THF (300 mL) maintained at -78° C. under an atmosphere of nitrogen. The mixture was stirred for 45 minutes and [3-(bromomethyl)-phenoxy]dimethyl(1,1-dimethylethyl)silane (l6.77 g, 50 mmol) added dropwise. After 10 minutes, the mixture was poured onto water, extracted with CH2Cl2, the extracts combined and dried over sodium sulfate. Evaporation of the solvent left an oil which was dissolved in THF (75 mL) and a solution of tetra-n-butylammonium fluoride (l7.22 g, 66mol) in THF (65 mL) added. The solution was stirred at room temperature for 30 minutes, the solvent evaporated and the residue diluted with water. After addition of 2N HCl solution (about 20 mL) to pH=5, the mixture was extracted with CH2Cl 2 The combined extracts were dried over sodium sulfate, concentrated in vacuo and the residual material chromatographed on a column of silica gel. Elution with a mixture of diethyl ether and hexanes (1.0 gave 3-[2-[1-(1-ethoxyethyl)-4,5-diphenyl-1H-imidazol-2-yl]ethyl]-phenol (8.l8 g, 39%), mp 165.5°-167° C. after recrystallization from a mixture of CH2Cl2 and hexanes.

Workup

  1. waitAfter 10 minutes
  2. additionthe mixture was poured onto water
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent
  6. waitleft an oil which
  7. dissolutionwas dissolved in THF (75 mL)
  8. stirringThe solution was stirred at room temperature for 30 minutes
  9. customthe solvent evaporated
  10. additionthe residue diluted with water
  11. additionAfter addition of 2N HCl solution (about 20 mL) to pH=5
  12. extractionthe mixture was extracted with CH2Cl 2 The combined extracts
  13. dry with materialwere dried over sodium sulfate
  14. concentrationconcentrated in vacuo
  15. customthe residual material chromatographed on a column of silica gel
  16. washElution
  17. additionwith a mixture of diethyl ether and hexanes (1.0

Sources & evidence

ORD record
ord-9cf3da07787a4b96ac72969c2137a096
Source dataset
uspto-grants-1991_04
Patent number
US05011851

Reaction notes

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