1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → 1-ethyl-4-fluoro-2-naphthalen-1-yl-1H-imidazole

HRID 12467

Reaction equation

HRID 12467 reaction equation
[CH2:1]([N:3]1[C:7]([Si](C)(C)C)=[C:6]([F:12])[N:5]=[C:4]1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([N:3]1[CH:7]=[C:6]([F:12])[N:5]=[C:4]1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH3:2]

Participants

4

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 686294501-ethyl-4-fluoro-2-naphthalen-1-yl-5-trimethylsilanyl-1H-imidazole

Product 1

HCID 593377711-ethyl-4-fluoro-2-naphthalen-1-yl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude 1-ethyl-4-fluoro-2-naphthalen-1-yl-5-trimethylsilanyl-1H-imidazole (5.49 g) is dissolved in THF (75 ml), and to the solution is added tetrabutylammonium fluoride hydrate (5.4 g, 20.6 mmol, 1.2 eq.). The resulting mixture is stirred at rt for 4 hr. The organic solvent is evaporated under reduced pressure, and the residue is dissolved in EtOAc (150 ml), washed with water and brine, and dried over Na2SO4. Concentration and purification through silica gel chromatography (hexanes/EtOAc, from 8:1 to 4:1) affords 1-ethyl-4-fluoro-2-naphthalen-1-yl-1H-imidazole. LCMS 241 (M+1).

Workup

  1. customThe organic solvent is evaporated under reduced pressure
  2. dissolutionthe residue is dissolved in EtOAc (150 ml)
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration and purification through silica gel chromatography (hexanes/EtOAc, from 8:1 to 4:1)

Sources & evidence

ORD record
ord-a55c86c65da04b15a979060a6498a635
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Linked notes

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