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

HRID 2179849ノート

反応式

HRID 2179849 の反応式
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

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 75806Tricyclohexylphosphine触媒HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

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”.

後処理

  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

出典と根拠

ORDレコード
ord-56031cb56adf4e81b66864a019be5b44
出典データセット
uspto-grants-2015_06
特許番号
US09070885B2

反応ノート

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