Sodium Acetate → HCID 59797508, compound

HRID 33919Notes

Reaction equation

HRID 33919 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].C([O-])(=O)C.[NH4+:10].[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=O)[CH:26](Br)[C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)(=O)C>[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:10]=[C:1]([CH3:2])[O:4][C:26]=2[C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 517165Ammonium AcetateHCID 59797501HCID 59797501, compound

Product 1

HCID 59797508HCID 59797508, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of sodium acetate (323 mg, 2.38 mmol) and ammonium acetate (304 mg, 3.95 mmol) in acetic acid (10 mL) was added 1-(4-(benzyloxy)phenyl)-2-bromo-2-(pyridin-4-yl)ethanone (302 mg, 0.79 mmol). The resulting mixture was then refluxed for 48 h. After removal of the solvent under vacuum, the residue was dissolved in ethyl acetate and the solution was washed with satd NaHCO3. The organic phase was dried and concentrated in vacuum to give an oil, which was purified via silica gel chromatography (1:3 EtOAc/n-hexane) to provide 111 mg (41%) of the title compound. 1H NMR (400 MHz, CDCl3) δ: 2.58 (s, 3H), 5.15 (s, 2H), 7.01 (d, 2H), 7.39 (m, 7H), 7.56 (d, 2H), 8.57 (d, 2H). MS m/z: 343 [M+1]+.

Workup

  1. temperatureThe resulting mixture was then refluxed for 48 h
  2. customAfter removal of the solvent under vacuum
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washthe solution was washed with satd NaHCO3
  5. customThe organic phase was dried
  6. concentrationconcentrated in vacuum
  7. customto give an oil, which
  8. customwas purified via silica gel chromatography (1:3 EtOAc/n-hexane)

Sources & evidence

ORD record
ord-2e46ac59a01241ad9ecd562421c317d1
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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