Ethanol → 9-(Naphthalen-1-yl)-10-(7-phenylnaphthalen-2-yl)anthracene

HRID 2179849노트

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HRID 2179849 반응식
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:17]3[C:18]4[C:23]([C:24](C5C6C(=CC=CC=6)C=CC=5)=[C:25]5[C:30]=3[CH:29]=[CH:28][CH:27]=[CH:26]5)=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:12][CH:13]=2)[CH:8]=1)(=O)=O.[C:43]1(B(O)O)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:60](O)[CH3:61]>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.[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.CO.O>[C:43]1([C:24]2[C:23]3[C:18]([C:17]([C:11]4[CH:12]=[CH:13][C:14]5[C:9](=[CH:8][C:7]([C:61]6[CH:60]=[CH:13][CH:12]=[CH:11][CH:10]=6)=[CH:16][CH:15]=5)[CH:10]=4)=[C:30]4[C:25]=2[CH:26]=[CH:27][CH:28]=[CH:29]4)=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:48]2[C:47](=[CH:16][CH:7]=[CH:8][CH:9]=2)[CH:46]=[CH:45][CH:44]=1

참가 물질

10

반응물 4

HCID 702EthanolHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 867013487-(10-(Naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate

생성물 1

HCID 867013499-(Naphthalen-1-yl)-10-(7-phenylnaphthalen-2-yl)anthracene

시약·촉매·용매 5

HCID 75806Tricyclohexylphosphine촉매HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 887Methanol용매HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

Under the nitrogen atmosphere, (7-(10-(naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate (3.0 g) as the fifth intermediate compound, phenylboronic acid (0.8 g), bis(dibenzylideneacetone)palladium (0) (Pd(dba)2) (0.03 g), tricyclohexyl phosphine (PCy3) (0.03 g), potassium phosphate (2.2 g), and a mixture solvent (22 ml) of toluene, ethanol, and water (toluene/ethanol/water=9/1/1 (volume ratio)) were added to a flask and refluxed for 2.5 hours. Once the heating is completed, the reaction solution was cooled to room temperature and added with methanol. The precipitates were collected by suction filtration. The obtained solid was washed with water followed by methanol, and washed further with ethyl acetate. The obtained crude product was dissolved in toluene, and colored components were removed by passing through an active carbon short column. After re-crystallization with chlorobenzene, 9-(naphthalen-1-yl)-10-(7-phenylnaphthalen-2-yl)anthracene (1.2 g) was obtained as the target compound represented by Formula (1-1). The scheme is shown in the following “Reaction 7”.

후처리

  1. temperaturerefluxed for 2.5 hours
  2. filtrationThe precipitates were collected by suction filtration
  3. washThe obtained solid was washed with water
  4. washwashed further with ethyl acetate
  5. customThe obtained crude product
  6. customcolored components were removed
  7. customAfter re-crystallization with chlorobenzene

출처 및 근거

ORD 기록
ord-56031cb56adf4e81b66864a019be5b44
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09070885B2

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