Ethyl Acetate → HCID 57847745, compound

HRID 736008Notes

Reaction equation

HRID 736008 reaction equation
F[C:2]1[CH:7]=[C:6]([CH:8]([CH2:17][C:18](=O)[C:19]([CH3:22])([CH3:21])[CH3:20])[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)C=C[N:3]=1.[C:24]([O-:27])(=O)[CH3:25].[NH4+:28].C([O-])(O)=O.[Na+].CCOC(C)=O>C(O)(=O)C>[C:19]([C:18]1[NH:28][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:8]([C:6]2[CH:7]=[CH:2][NH:3][C:24](=[O:27])[CH:25]=2)[CH:17]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 57847746HCID 57847746, compound

Product 1

HCID 57847745HCID 57847745, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(2-fluoropyridin-4-yl)-5,5-dimethyl-1-phenylhexane-1,4-dione (200 mg, 0.6 mmol) and ammonium acetate (329 mg, 3.8 mmol) in acetic acid (3 mL) was heated at reflux for 18 h. Upon cooling to RT the solution was slowly added to a mixture of sat'd aqueous NaHCO3 (40 mL) and EtOAc (40 mL). The mixture was stirred for 15 min. and the organic layer then collected. The aqueous layer was extracted with ethyl acetate (25 mL) and the organic layers combined, washed with sat'd aqueous NaHCO3, H2O and brine, dried (MgSO4) and concentrated. The product was purified by flash chromatography using EtOAc-MeOH (100:0→95:5) as eluant to give the pure product as a cream solid (144 mg, 78%).

Workup

  1. temperatureat reflux for 18 h
  2. customthe organic layer then collected
  3. extractionThe aqueous layer was extracted with ethyl acetate (25 mL)
  4. washwashed with sat'd aqueous NaHCO3, H2O and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-709d0914fee44fafb5e541ba536db461
Source dataset
uspto-grants-2009_09
Patent number
US07593820B2

Reaction notes

Loading…