Water → Methyl3-(2-cyanobenzo[b]thiophen-5-yl)acrylate

HRID 2288060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2288060
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[C:14]([C:16]1[S:20][C:19]2[CH:21]=[CH:22][C:23](I)=[CH:24][C:18]=2[CH:17]=1)#[N:15].O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:6][O:5][C:1](=[O:4])[CH:2]=[CH:3][C:23]1[CH:22]=[CH:21][C:19]2[S:20][C:16]([C:14]#[N:15])=[CH:17][C:18]=2[CH:24]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 187029595-Iodobenzo[b]thiophene-2-carbonitrile

Produkt 1

HCID 54151697Methyl3-(2-cyanobenzo[b]thiophen-5-yl)acrylateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Methyl acrylate (2 g), triethylamine (2.35 g) and palladium acetate (0.05 g) was added to 2-cyano-5-iodobenzo[b]thiophene (4.8 g) in DMF (25 ml) and the mixture was stirred under argon at 90° C. for 30 minutes. The mixture was allowed to cool and then added to water (50 ml). The solid which precipitated was collected by filtration and dissolved in chloroform. Activated charcoal was added and the mixture filtered and the filtrate dried (MgSO4). Solvent was removed by evaporation to give methyl3-(2-cyanobenzo[b]thiophen-5-yl)acrylate (2.5 g); NMR (d6 -DMSO): 3.75 (s, 3H), 6.7 (d, 1H), 7.8 (d, 1H), 8.0 (dd, 1H), 8.2 (d, 1H), 8.3 (d, 1H), 8.85 (s, 1H).

Aufarbeitung

  1. temperatureto cool
  2. customThe solid which precipitated
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in chloroform
  5. additionActivated charcoal was added
  6. filtrationthe mixture filtered
  7. dry with materialthe filtrate dried (MgSO4)
  8. customSolvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-e892c006547f43a9b921d7adfb79c264
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06087336

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