Sodium Hydroxide → HCID 178419940, compound

HRID 748661Notes

Reaction equation

HRID 748661 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11][C:12]2[N:13]=[CH:14][N:15](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:16]=2)=[CH:2]1.[OH-].[Na+]>C(O)(=O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11][C:12]2[N:13]=[CH:14][NH:15][CH:16]=2)=[CH:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69206645HCID 69206645, compound

Product 1

HCID 178419940HCID 178419940, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4-(1-Benzofuran-3-yl-ethyl)-1-trityl-1H-imidazole (Intermediate I4) (0.52 g) in acetic acid (10 mL) and water (5 mL) was heated to reflux for 1 h. The mixture was cooled to rt and the pH was adjusted with 2M NaOH until basic. The aqueous layer was extracted with dichloromethane. The organic layers were combined, dried over MgSO4 and filtered through paper. The solvent was removed under a vacuum. The residue was purified by chromatography on silical gel with 2.5% NH3-MeOH: CH2Cl2 to give 4-(1-benzofuran-3-yl-ethyl)-1H-imidazole Intermediate I5) 0.29 g.

Workup

  1. temperatureto reflux for 1 h
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialdried over MgSO4
  4. filtrationfiltered through paper
  5. customThe solvent was removed under a vacuum
  6. customThe residue was purified by chromatography on silical gel with 2.5% NH3-MeOH

Sources & evidence

ORD record
ord-6feb1ebc25ea49b1a71df92e22d6b04d
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Reaction notes

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