Ammonium Acetate → HCID 9878343, compound

HRID 1650675Notes

Reaction equation

HRID 1650675 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:17][C:18](=O)[CH3:19])[CH:9]([C:14](=O)[CH3:15])[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:25]>C(O)(=O)C.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[CH3:15][C:14]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:17]=[C:18]([CH3:19])[N:25]=1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 14460132HCID 14460132, compound

Product 1

HCID 9878343HCID 9878343, compound

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of 28.0 g (100 mmol) of methyl 3-(4-fluorophenyl)-2-(1-oxoethyl)-5-oxohexanoate (=Xa from Example 1), 120 g of ammonium acetate and 120 g of iron(III) chloride hexahydrate in 1000 ml of glacial acetic acid was refluxed, with stirring, until the precursor could no longer be detected by thin-layer chromatography (4 h). The mixture was cooled and then filtered, and the solid residue was washed with ethanol and toluene. The filtrate was evaporated and then the residue was suspended in water, the pH was adjusted to 8-9 by addition of solid sodium bicarbonate, and the mixture was extracted several times with ether. The combined extracts were washed with saturated NaCl, dried over MgSO4 and evaporated. Purification of the crude product by column chromatography (silica gel, cyclohexane/ethyl acetate 2:1) provided 23.6 g (91%) of XVa in the form of white crystals.

Workup

  1. temperaturewas refluxed
  2. customcould no longer be detected by thin-layer chromatography (4 h)
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe solid residue was washed with ethanol and toluene
  6. customThe filtrate was evaporated
  7. additionthe pH was adjusted to 8-9 by addition of solid sodium bicarbonate
  8. extractionthe mixture was extracted several times with ether
  9. washThe combined extracts were washed with saturated NaCl
  10. dry with materialdried over MgSO4
  11. customevaporated
  12. customPurification of the crude product by column chromatography (silica gel, cyclohexane/ethyl acetate 2:1)
  13. customprovided 23.6 g (91%) of XVa in the form of white crystals

Sources & evidence

ORD record
ord-fa56086daefa4c019baf6a646e172d04
Source dataset
uspto-grants-1990_05
Patent number
US04925852

Reaction notes

Loading…