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Potassium Carbonate → methyl (E)-3-[4-(4-methylphenyl)thiophen-2-yl)acrylate

HRID 2228212
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2228212
C/[C:2](=[CH:6]\[C:7]1[S:8][CH:9]=[C:10](Br)[CH:11]=1)/[C:3]([OH:5])=[O:4].B([O-])([O-])O[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.[C:24](=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.O.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>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([C:10]2[CH:11]=[C:7](/[CH:6]=[CH:2]/[C:3]([O:5][CH3:24])=[O:4])[S:8][CH:9]=2)=[CH:16][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 866453334-Methylphenyl borateHCID 86756172methyl (E)-3-(4-bromothiophen-2-yl)acrylic acid

Produkt 1

HCID 86756171methyl (E)-3-[4-(4-methylphenyl)thiophen-2-yl)acrylateAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 66602552Toluene-ethanol waterLösungsmittel

Versuchsvorschrift

Under argon atmosphere, a solution of methyl (E)-3—(4-bromothiophen-2-yl)acrylic acid (3.0 g), 4-methylphenyl borate (1.82 g) and potassium carbonate (3.36 g) in toluene-ethanol-water (120-12-12 ml) was stirred at room temperature for 1 hour. To the reaction mixture was added tetrakistriphenylphosphinepalladium (0.42 g), and the mixture was refluxed for 24 hours and cooled to room temperature. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:9→1:5→1:2) to give methyl (E)-3-[4—(4-methylphenyl)thiophen-2-yl)acrylate (2.40 g) as pale yellow crystals.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 24 hours
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate/hexane=1:9→1:5→1:2)

Quellen und Nachweise

ORD-Eintrag
ord-27b72d26eb6549a58d2a7479970951b0
Quelldatensatz
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06413947B1

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