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

HRID 1421112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421112
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d11e3ff76f1b492dad36cb286a9e7fd2
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06072073

Notizen zur Reaktion

Wird geladen…