Cesium carbonate → HCID 86657857、化合物

HRID 1257560ノート

反応式

HRID 1257560 の反応式
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:21]1[C:29]([CH3:30])=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[CH:24][CH2:25]2>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([C:21]2[C:29]([CH3:30])=[CH:28][CH:27]=[C:26]3[C:22]=2[CH:23]=[CH:24][CH2:25]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2545321-Naphthaleneboronic acidHCID 58444066HCID 58444066、化合物

生成物 1

HCID 86657857HCID 86657857、化合物収率 87%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

1-Naphthylboronic acid (10 g, 58.1 mmol) was dissolved in dimethoxyethane (150 mL), and aqueous solution (100 mL) of cesium carbonate (25.3 g, 78 mmol), 4-bromo-5-methylindene (8.1 g, 39 mmol), tetrakis(triphenylphosphine)palladium (1.8 g) were sequentially added. Solution was reacted for 21 hours while heating under reflux, then, reaction solution was poured into 1N hydrochloric acid-ice water, and after stirring, reaction solution was extracted with diethyl ether. Organic layer was washed with magnesium sulfate, then, solvent was distilled off under reduced pressure to obtain the crude product. This was purified by silica-gel column chromatography to obtain the desired 4-(1-naphthyl)-5-methylindene (8.6 g, yield: 87%).

後処理

  1. customSolution was reacted for 21 hours
  2. temperaturewhile heating
  3. temperatureunder reflux
  4. customreaction solution
  5. customreaction solution
  6. extractionwas extracted with diethyl ether
  7. washOrganic layer was washed with magnesium sulfate
  8. distillationsolvent was distilled off under reduced pressure
  9. customto obtain the crude product
  10. customThis was purified by silica-gel column chromatography

出典と根拠

ORDレコード
ord-1d3b447ec8ed4b7d8e55538fb76c83eb
出典データセット
uspto-grants-2013_06
特許番号
US08461365B2

反応ノート

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