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

HRID 1421112ノート

反応式

HRID 1421112 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 11096728Alpha-(4-methoxyphenyl)propiophenone収率 60%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d11e3ff76f1b492dad36cb286a9e7fd2
出典データセット
uspto-grants-2000_06
特許番号
US06072073

反応ノート

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