Ethanol → Anthracene

HRID 2179851ノート

反応式

HRID 2179851 の反応式
FC(F)(F)S(OC1C=CC2C(=CC([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)=CC=2)C=1)(=O)=O.C1(C2C=CC(B(O)O)=CC=2)C2C(=CC=CC=2)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)C>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>[CH:19]1[C:18]2[C:23](=[CH:24][C:25]3[C:30]([CH:17]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:22]=[CH:21][CH:20]=1

参加物

10

反応物 4

HCID 702EthanolHCID 62657Potassium Phosphate, TribasicHCID 441193994-(1-Naphthyl)phenylboronic Acid (contains varying amounts of Anhydride)HCID 867013487-(10-(Naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate

生成物 1

HCID 8418Anthracene収率 281.4%

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, (4-(naphthalen-1-yl)phenyl)boronic acid (1.9 g), bis(dibenzylideneacetone)palladium (0) (Pd(dba)2) (0.03 g), tricyclohexyl phosphine (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 6.5 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 a silica gel short column. The solvent was distilled off under reduced pressure. The obtained oily phase substance was added with ethyl acetate and the precipitated products were collected by suction filtration to give 9-(naphthalen-1-yl)-10-(7-(naphthalen-1-yl)phenyl)naphthalen-2-yl)anthracene (2.6 g) as the target compound represented by Formula (1-21). The scheme is illustrated in the following “Reaction 9”.

後処理

  1. temperaturerefluxed for 6.5 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. distillationThe solvent was distilled off under reduced pressure
  8. additionThe obtained oily phase substance was added with ethyl acetate
  9. filtrationthe precipitated products were collected by suction filtration

出典と根拠

ORDレコード
ord-b115ea772ac14afda87a157490d25ca9
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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