Ethyl Acetate → methyl (E)-3-[5-(4-tert-butylphenyl)thiophen-2-yl]acrylate

HRID 1277242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1277242
Br[C:2]1[S:6][C:5](/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.B([O-])([O-])O[C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C(O)C.O>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:2]2[S:6][C:5](/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=2)=[CH:16][CH:17]=1)([CH3:24])([CH3:23])[CH3:22]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 25417100(E)-methyl 3-(5-bromothiophen-2-yl)acrylateHCID 867561654-Tert-butylphenyl borate

Produkt 1

HCID 86756177methyl (E)-3-[5-(4-tert-butylphenyl)thiophen-2-yl]acrylateAusbeute 85,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86587398Ethanol toluene waterLösungsmittel

Versuchsvorschrift

Under argon atmosphere, a solution of methyl (E)-3-(5-bromothiophen-2-yl)acrylate (0.23 g), 4-tert-butylphenyl borate (0.3 g) and potassium carbonate (0.26 g) in toluene/ethanol/water (20/2/2 ml) was stirred at room temperature for 1 hour. To the mixture was added tetrakistriphenylphosphine palladium (32 mg), and the mixture was refluxed for 18 hours and then cooled to room temperature. To the organic layer was added ethyl acetate, and the mixture was washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/hexane=1:9) to give pale yellow crystals of methyl (E)-3-[5-(4-tert-butylphenyl)thiophen-2-yl]acrylate (240 mg). This compound was used for the following reaction, without subjecting further purification.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 18 hours
  2. washthe mixture was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationUnder reduced pressure, the mixture was concentrated
  5. customthe residue was purified with column chromatography (ethyl acetate/hexane=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-9a5505ea241441868d2b213529781e4f
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06166006

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