Water → HCID 86598167, compound

HRID 458432Notes

Reaction equation

HRID 458432 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10](=O)[CH2:11][C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13].C([O-])(=O)C.[NH4+:23].O>C1(C)C=CC=CC=1>[NH2:23]/[C:10](/[CH2:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])=[CH:11]/[C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 517165Ammonium AcetateHCID 18441987HCID 18441987, compound

Product 1

HCID 86598167HCID 86598167, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Allyl 4-(2,4-difluorophenyl)-3-oxobutanoate (5.0 g, 19.67 mmol) and ammonium acetate (7.58 g, 98.33 mmol) were refluxed in toluene (20 mL) for 2 h with azeotropic removal of H2O and then cooled and concentrated. The residue was redissolved in Et2O and the organics washed with 1N HCl (2×), H2O, brine, and then dried (Na2SO4), filtered and concentrated to give 5.0 g (100% yield) of the title compound as a yellow oil: 1H NMR (CDCl3, 400 MHz) δ 7.25–7.14 (m, 1H), 6.63 (dd, J=16.1, 7.9 Hz, 2H), 5.97–5.88 (m, 1H), 5.28 (dd, J=17.2, 1.5 Hz, 1H), 5.19 (dd, J=10.2, 1.1 Hz, 1H), 4.60 (s, 1H), 4.55 (d, J=5.7 Hz, 2H), 3.43 (s, 2H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in Et2O
  4. washthe organics washed with 1N HCl (2×), H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-162d75e1ee0540b2aaf909b504785ff2
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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