Cesium carbonate → HCID 86657857, Verbindung

HRID 1257560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257560
[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

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 2545321-Naphthaleneboronic acidHCID 58444066HCID 58444066, Verbindung

Produkt 1

HCID 86657857HCID 86657857, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1d3b447ec8ed4b7d8e55538fb76c83eb
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461365B2

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