Ammonium Acetate → HCID 66862226, compound

HRID 2368633Notes

Reaction equation

HRID 2368633 reaction equation
[OH:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)=[CH:3][C:4](=O)[CH:5]([O:7][CH3:8])[CH3:6].C([O-])(=O)C.[NH4+:24]>>[NH2:24][C:4]([CH:5]([O:7][CH3:8])[CH3:6])=[CH:3][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)=[O:1]

Participants

3

Reactant 2

HCID 517165Ammonium AcetateHCID 66862425HCID 66862425, compound

Product 1

HCID 66862226HCID 66862226, compound

Procedure

10.0 g 1-Hydroxy-4-methoxy-1-(4-trifluoromethyl-phenyl)-pent-1-en-3-one are dissolved in 100 ml ethanole. 4.7 g of Ammonium acetate are added and the mixture is heated for four hours to reflux. Then the solvent is evaporated in vacuo, the residue is partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The phases are separated and the aqueous phase is twice extracted with dichloromethane. The combined organic phases are dried with magnesium sulphate, the solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethylacetate 90:10 to 50:50).

Workup

  1. temperaturethe mixture is heated for four hours
  2. temperatureto reflux
  3. customThen the solvent is evaporated in vacuo
  4. customthe residue is partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane
  5. customThe phases are separated
  6. extractionthe aqueous phase is twice extracted with dichloromethane
  7. dry with materialThe combined organic phases are dried with magnesium sulphate
  8. customthe solvents are evaporated in vacuo
  9. customthe residue is chromatographed on silica gel (cyclohexane/ethylacetate 90:10 to 50:50)

Sources & evidence

ORD record
ord-79cda5ec43724d4e8d93782a33519055
Source dataset
uspto-grants-2014_04
Patent number
US08703793B2

Reaction notes

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