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

HRID 1062928
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1062928
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.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1C1C=CC=CC=1P(C1C=CC=CC=1C1C=CC=CC=1C)C1C=CC=CC=1C1C=CC=CC=1C>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:14]3[O:13][CH:17]=[CH:16][CH:15]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 158697837-Bromo-2-methyl-2,3-dihydro-1H-inden-1-one

Produkt 1

HCID 221733462-Methyl-7-(2-furanyl)-1-indanoneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845
palladium(II) acetate
Katalysator
HCID 22172997Tris(o-tolylphenyl)phosphineKatalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Using a method similar to Example 22, 33.7 g (0.15 mol) of (2), 18.5 g (0.165 mol) of furanylboronic acid and 34.9 g (0.33 mol) of sodium carbonate were placed in 570 ml of dimethoxyethane and 180 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 675 mg (3 mmol) of palladium acetate and 1.83 g (6 mmol) of tris(o-tolylphenyl)phosphine were added and the reaction mixture was stirred for 2 hours at 80° C. After addition of 450 ml of water, the mixture was extracted 4 times with 300 ml each time of diethyl ether, the ether phase was washed twice with 200 ml each time of water and dried over magnesium sulfate. Removal of the solvent gave 27.06 g of (23) as an oil.

Aufarbeitung

  1. custom180 ml of water in the reaction vessel, the mixture was degassed a number of times
  2. extractionthe mixture was extracted 4 times with 300 ml each time of diethyl ether
  3. washthe ether phase was washed twice with 200 ml each time of water
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-f391ce9ab5a248d795610030d0b94aff
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06963017B2

Notizen zur Reaktion

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