Cesium carbonate → Ethyl 4-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

HRID 1097376노트

반응식

HRID 1097376 반응식
[CH:1]1[C:12]2=[C:13]3[CH:8]([CH2:9][CH2:10][CH2:11]2)[CH2:7][CH2:6][CH2:5][C:4]3=[CH:3][C:2]=1[NH2:14].I[C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:1]1[C:12]2=[C:13]3[CH:8]([CH2:9][CH2:10][CH2:11]2)[CH2:7][CH2:6][CH2:5][C:4]3=[CH:3][C:2]=1[NH:14][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 142891Ethyl 4-iodobenzoateHCID 634876Binap, (A+-)-HCID 58420580HCID 58420580, 화합물

생성물 1

HCID 66811225Ethyl 4-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate수율 36.6%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

5,6,6a,7,8,9-Hexahydro-4H-2-phenalenylamine (0.250 g) and ethyl 4-iodobenzoate (0.360 g) were dissolved in anhydrous toluene (5 ml), the solution was added with tris(dibenzylideneacetone)dipalladium (0.024 g), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.036 g), and cesium carbonate (0.455 g), and the mixture was stirred overnight at 80° C. under an argon flow. The reaction mixture was left to cool, and then poured into ice water, and the mixture was extracted with diethyl ether. The organic layer was washed successively with 2 N aqueous hydrochloric acid, water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:50) to obtain the title compound (0.160 g, yield: 36%). The compound was recrystallized from chloroform-n-hexane to obtain colorless needles (melting point: 154-155° C.).

후처리

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe organic layer was washed successively with 2 N aqueous hydrochloric acid, water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:50)

출처 및 근거

ORD 기록
ord-ef64d016c6dd4fb5b881a6f293a6d4ce
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143260B2

반응 노트

불러오는 중…