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Water → 4-Ethoxycarbonyl-5-(2-trimethylsilylethynyl)thiazole

HRID 1799699
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1799699
Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C.[C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])#[CH:20].O>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[CH2:10]([O:9][C:7]([C:3]1[N:4]=[CH:5][S:6][C:2]=1[C:20]#[C:19][Si:21]([CH3:24])([CH3:23])[CH3:22])=[O:8])[CH3:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 12361218Ethyl 5-bromo-1,3-thiazole-4-carboxylate

Produkt 1

HCID 592179544-Ethoxycarbonyl-5-(2-trimethylsilylethynyl)thiazole

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 6228DimethylformamideLösungsmittel
HCID 8058HexaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

5-Bromo-4-ethoxycarbonylthiazole (18.64 g) was dissolved in 80 ml of DMF. Triethylamine (22 ml), 16.7 ml of ethynyltrimethylsilane, 960 mg of copper(I) iodide, and 1.11 g of bis(triphenylphosphine)palladium(II) dichloride were added in that order to the solution, and the mixture was stirred at 90° C. under an argon atmosphere for one hr. Water (80 ml), 160 ml of ethyl acetate and 160 ml of hexane were added to the reaction solution, and the mixture was washed with (brine+aqueous hydrochloric acid), sodium bicarbonate water, and brine in that order. Activated carbon and anhydrous magnesium sulfate were added to the organic layer, and the mixture was filtered and was concentrated under the reduced pressure to give 16.45 g of the title compound.

Aufarbeitung

  1. washthe mixture was washed with (brine+aqueous hydrochloric acid), sodium bicarbonate water, and brine in that order
  2. additionActivated carbon and anhydrous magnesium sulfate were added to the organic layer
  3. filtrationthe mixture was filtered
  4. concentrationwas concentrated under the reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-56b55940e5db49e3a165b8de5069d733
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08344154B2

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