1-Phenyl-1-propanone → Alpha-(4-methoxyphenyl)propiophenone

HRID 1421112Notes

Reaction equation

HRID 1421112 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].[C:11]1(C)[CH:16]=[CH:15]C=[CH:13][C:12]=1C1(C)C=CC(S([O-])(=O)=O)=CC1.C[C:30]([O-:33])(C)C.[Na+].[CH3:35]C1C=CC(C2C=C(S([O-])(=O)=O)C=CC=2C)=CC=1>O1CCOCC1.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:30][O:33][C:11]1[CH:16]=[CH:15][C:3]([CH:2]([CH3:35])[C:1]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 71481-Phenyl-1-propanone2×HCID 23676156Sodium t-butoxideHCID 86755453p-TolyltosylateHCID 867554554-Methylphenyl-p-toluene sulfonate

Product 1

HCID 11096728Alpha-(4-methoxyphenyl)propiophenoneYield 60%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Reaction of propiophenone with p-tolyltosylate: Pd(OAc)2 (9.0 mg, 0.040 mmol), ligand (27.1 mg, 0.050 mmol), NaOtBu (144 mg, 1.50 mmol) and 4-methylphenyl-p-toluene sulfonate (262 mg, 1.00 mmol) were suspended in 1 mL of dioxane in a screw-capped vial. The vial was sealed with a cap containing a PTFE septum and removed from the dry box. Propiophenone (132 mg, 1.10 mmol) was added to the reaction mixture by syringe. The reaction mixture was stirred at 100° C. and monitored by GC analysis. The crude reaction was diluted with ether and washed with 1N HCl, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel (hexane/EtOAc=95/5) to give 135 mg (60%) of 2-(4-Methoxyphenyl)-1-phenyl-1-propanone.

Workup

  1. customThe vial was sealed with a cap
  2. customremoved from the dry box
  3. customThe crude reaction
  4. washwashed with 1N HCl, water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel (hexane/EtOAc=95/5)

Sources & evidence

ORD record
ord-d11e3ff76f1b492dad36cb286a9e7fd2
Source dataset
uspto-grants-2000_06
Patent number
US06072073

Reaction notes

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