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

HRID 1421112노트

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HRID 1421112 반응식
[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

참가 물질

8

반응물 4

HCID 71481-Phenyl-1-propanone2회HCID 23676156Sodium t-butoxideHCID 86755453p-TolyltosylateHCID 867554554-Methylphenyl-p-toluene sulfonate

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d11e3ff76f1b492dad36cb286a9e7fd2
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06072073

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