Citric Acid → 2-(benzamido)-4-((E)-2-(2-methylphenyl)vinyl)benzoic acid

HRID 1673387ノート

反応式

HRID 1673387 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].C(=O)([O-])[O-].[Cs+].[Cs+].[C:15]([NH:23][C:24]1[CH:36]=[C:35]([CH:37]=[CH2:38])[CH:34]=[CH:33][C:25]=1[C:26]([O:28]C(C)(C)C)=[O:27])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(P([Pd+])C2CCCCC2)CCCCC1.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:15]([NH:23][C:24]1[CH:36]=[C:35](/[CH:37]=[CH:38]/[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH3:8])[CH:34]=[CH:33][C:25]=1[C:26]([OH:28])=[O:27])(=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

9

反応物 4

HCID 311Citric AcidHCID 51282-IodotolueneHCID 10796Cesium carbonateHCID 67343635Tert-butyl 2-(benzamido)-4-vinylbenzoate

生成物 1

HCID 578793232-(benzamido)-4-((E)-2-(2-methylphenyl)vinyl)benzoic acid

試薬・触媒・溶媒 4

HCID 74236Tetrabutylammonium Bromide触媒HCID 178527697HCID 178527697、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

0.031 mL of 2-iodotoluene, 81 g of cesium carbonate, 12 mg of tetrabutylammonium bromide and 19 mg of polymer supported di(acetato) dicyclohexylphosphino palladium(II) were added to 1.0 mL of toluene solution containing 40 mg of tert-butyl 2-(benzamido)-4-vinylbenzoate at room temperature and stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added, the organic layer was separated, and the solvent was evaporated under reduced pressure after washed with 10% citric acid aqueous solution, 5 mL of trifluoroacetic acid was added to the obtained residue and stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure and the obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 65-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to obtain 2.8 mg of 2-(benzamido)-4-((E)-2-(2-methylphenyl)vinyl)benzoic acid as while solid.

後処理

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customthe organic layer was separated
  3. customthe solvent was evaporated under reduced pressure
  4. washafter washed with 10% citric acid aqueous solution, 5 mL of trifluoroacetic acid
  5. additionwas added to the obtained residue
  6. stirringstirred at room temperature for 1 hour
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 65-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution]

出典と根拠

ORDレコード
ord-02f7dec6e2f74c98ab660c388c4a68d7
出典データセット
uspto-grants-2011_08
特許番号
US07999132B2

反応ノート

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