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Water → 2-Methyl-7-(2-pyridyl)-1-indanone

HRID 1062929
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1062929
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.C[Sn](C)(C)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.O>O1CCCC1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd]>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 11021057Pyridine, 2-(trimethylstannyl)-HCID 158697837-Bromo-2-methyl-2,3-dihydro-1H-inden-1-one

Produkt 1

HCID 221730322-Methyl-7-(2-pyridyl)-1-indanoneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11104995
trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

16.9 g (75 mmol) of (2) and 20 g (90 mmol) of 2-trimethylstannylpyridine were placed in 165 ml of tetrahydrofuran in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 350 mg (0.37 mmol) of trans-di(μ-acetato)bis-[o-(di-o-tolylphosphino)benzyl]dipalladium (II) were added and the reaction mixture was refluxed for 24 hours. After addition of 200 ml of water, the mixture was extracted 4 times with 150 ml each time of diethyl ether, the ether phase was washed with 100 ml of water and 100 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent and drying for 24 hours at 0.1 mbar at 60° C. (removal of the trimethylstannyl bromide) gave 15.07 g of (24) as an oil.

Aufarbeitung

  1. customthe mixture was degassed a number of times
  2. temperaturethe reaction mixture was refluxed for 24 hours
  3. extractionthe mixture was extracted 4 times with 150 ml each time of diethyl ether
  4. washthe ether phase was washed with 100 ml of water and 100 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solvent
  7. customdrying for 24 hours at 0.1 mbar at 60° C. (
  8. customremoval of the trimethylstannyl bromide)

Quellen und Nachweise

ORD-Eintrag
ord-1f0ffe8533ad42a4b10ad19724346958
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06963017B2

Notizen zur Reaktion

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