Potassium Carbonate → 3-Phenyl-2,4-heptanedione

HRID 891070Notes

Reaction equation

HRID 891070 reaction equation
[CH3:1][C:2](=[O:10])[CH2:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7]C.I[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[C:12]1([CH:3]([C:4](=[O:9])[CH2:5][CH2:6][CH3:7])[C:2](=[O:10])[CH3:1])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 841922,4-Octanedione

Product 1

HCID 222446113-Phenyl-2,4-heptanedioneYield 48.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred mixture of 2,4-octanedione (568 mg, 4.0 mmol) and iodobenzene (408 mg, 2.0 mmol) in dimethylsulfoxide (10 mL) were added copper(I) iodide (380 mg, 2.0 mg) and potassium carbonate (1.10 g, 8.0 mmol). The mixture was heated at 120° C. for 4 h. The mixture was filtered through a pad of Celite and the filtrate was partitioned between ether and water. Organic layer was dried (Na2SO4) and the solvent was removed. The crude product was purified by TLC with hexane/ethyl acetate (4:1) to afford 199 mg (46%) of the title compound as colorless oil: 1H-NMR (CDCl3) δ 7.42-7.33 (3H, m), 7.18-7.15 (2H, m), 2.11 (2H, t, J=8.3 Hz), 1.87 (3H, s), 1.58-1.44 (3H, m), 1.25-1.16 (2H, m), 0.79 (3H, t, J=7.2 Hz).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customthe filtrate was partitioned between ether and water
  3. dry with materialOrganic layer was dried (Na2SO4)
  4. customthe solvent was removed
  5. customThe crude product was purified by TLC with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-785bbebae10540c7892a27c1dc122ae4
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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