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Sodium hydride → HCID 11175089, Verbindung

HRID 1434424
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1434424
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[C:9]([OH:11])[CH:10]=1.C([O:28][C:29]1[CH:34]=[CH:33][C:32](Br)=[CH:31][CH:30]=1)C1C=CC=CC=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[C:9]([CH:10]=1)[O:11][C:32]1[CH:33]=[CH:34][C:29]([OH:28])=[CH:30][CH:31]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 24758Sodium hydrideHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 11736683HCID 11736683, Verbindung

Produkt 1

HCID 11175089HCID 11175089, VerbindungAusbeute 20,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845
palladium(II) acetate
Katalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

The title compound was synthesized by referring to J. Am. Chem. Soc., 1999, 121 (18), 4369. To a suspension of 60% sodium hydride (600 mg) in toluene (50 ml) was added 5-methoxy-2-(3-methoxybenzyl)phenol (2.4 g), and the solution was stirred at 90° C. until generation of gas was stopped. The reaction solution was cooled to room temperature, then 1-benzyloxy-4-bromobenzene (2.6 g), palladium(II) acetate (112 mg), 2-(di-tert-butylphosphino)biphenyl (149 mg) were sequentially added thereto, and the solution was stirred for 18 hours and 50 minutes at 95° C. To the reaction solution was added water, the solution was extracted with ethyl acetate, then the insoluble material was filtered through celite pad, the filtrate was dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. Obtained by purifying the residue by silica gel column chromatography (hexane-ethyl acetate system), 2-(4-benzyloxy phenoxy)-4-methoxy-1-(3-methoxybenzyl)benzene (1.4 g) was used according to an analogous synthetic method to Example 22 to provide the title compound (690 mg).

Aufarbeitung

  1. customThe title compound was synthesized
  2. temperatureThe reaction solution was cooled to room temperature
  3. stirringthe solution was stirred for 18 hours and 50 minutes at 95° C
  4. extractionthe solution was extracted with ethyl acetate
  5. filtrationthe insoluble material was filtered through celite pad
  6. dry with materialthe filtrate was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customObtained
  9. customby purifying the residue by silica gel column chromatography (hexane-ethyl acetate system), 2-(4-benzyloxy phenoxy)-4-methoxy-1-(3-methoxybenzyl)benzene (1.4 g)

Quellen und Nachweise

ORD-Eintrag
ord-2f5d973f140d421180f70b40b343a2e5
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612114B2

Notizen zur Reaktion

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