Water → 2-Acetyl-5-(4-fluoro-phenyl)cyclohexane-1,3-dione

HRID 2046465Notes

Reaction equation

HRID 2046465 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[CH2:11][C:10](=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[C:16]([O-])(=[O:18])[CH3:17].[Na+].C(OCC)(=O)C.O>C(OC(=O)C)(=O)C>[C:16]([CH:11]1[C:12](=[O:14])[CH2:13][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:9][C:10]1=[O:15])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 7301365-(4-Fluorophenyl)cyclohexane-1,3-dione

Product 1

HCID 529508832-Acetyl-5-(4-fluoro-phenyl)cyclohexane-1,3-dione

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

5-(4-Fluorophenyl)cyclohexane-1,3-dione (500 mg, 2.4 mmol) and sodium acetate (200 mg, 2.4 mmol) were dissolved in acetic anhydride (5 ml) and heated in a sealed tube at 120° C. for 16 h. The reaction mixture was then allowed to cool to ambient temperature whereupon ethyl acetate (20 ml) and water (10 ml) were added. The organic phase was collected and washed 3 times with a saturated solution of sodium bicarbonate (3×15 ml). The organic phase was dried with MgSO4 and filtered. The solvent was removed under reduced pressure. The title compound was purified by column chromatography using ethyl acetate/heptane (1/3) as the eluent.

Workup

  1. additionwere added
  2. customThe organic phase was collected
  3. washwashed 3 times with a saturated solution of sodium bicarbonate (3×15 ml)
  4. dry with materialThe organic phase was dried with MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customThe title compound was purified by column chromatography

Sources & evidence

ORD record
ord-43dd97b478c44479b8f357cdcf866fd6
Source dataset
uspto-grants-2013_11
Patent number
US08592430B2

Reaction notes

Loading…