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Water → 1-[3-(3-Methoxypropoxy)-5-methylphenyl]ethanone

HRID 922450
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 922450
C(O[C:5]1[C:10]2[CH:11]=[CH:12][O:13][C:9]=2[CH:8]=[C:7]([C:14](OCC)=O)[CH:6]=1)(=O)C.[C:19](=[O:22])([O-])[O-].[K+].[K+].[CH3:25]B1OB(C)OB(C)O1.O.[O:35]1[CH2:40]COC[CH2:36]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:36][O:35][CH2:40][CH2:11][CH2:12][O:13][C:9]1[CH:10]=[C:5]([C:19](=[O:22])[CH3:25])[CH:6]=[C:7]([CH3:14])[CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574072TrimethylboroxineHCID 675451626-Benzofurancarboxylic acid, 4-(acetyloxy)-, ethyl ester

Produkt 1

HCID 683105641-[3-(3-Methoxypropoxy)-5-methylphenyl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of the compound obtained in the (1) (8.22 g) in 1,4-dioxane 9100 mL) were added potassium carbonate (8.6 g), trimethylboroxine (3.5 mL) and 1,1′-bis(diphenylphosphino)ferrocene dichloropalladium (II) (1.51 g), and the mixture was heated to stir at 110° C. for 2 hours. After cooling to room temperature, thereto was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=5/1) to give 1-[3-(3-methoxypropoxy)-5-methylphenyl]ethanone [REx(21-2)] (4.15 g) as a brown oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-094b9d722302499786841d5949b24691
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09278944B2

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