Triethylamine → 1-(4-Methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone

HRID 390769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390769
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].Br[C:8]1[S:12][C:11]([C:13](=[O:15])[CH3:14])=[CH:10][C:9]=1[CH3:16].C(N(CC)CC)C>CN(C=O)C.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.[Cu]I>[CH3:16][C:9]1[CH:10]=[C:11]([C:13](=[O:15])[CH3:14])[S:12][C:8]=1[C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 454803531-(5-Bromo-4-methylthiophen-2-yl)ethan-1-one

Produkt 1

HCID 674301401-(4-Methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Trimethylsilylacetylene (16 ml) is added to a solution of 1-(5-bromo-4-methyl-thiophen-2-yl)-ethanone (16.9 q, example 1, step A), Pd(PPh3)2Cl2 (3.78 g), CuI (1.46 g) and triethylamine (16 ml) in DMF (15 ml). After 3 hours at room temperature, the reaction is quenched with water and extracted three times with ethyl acetate. The organic phases are combined, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by filtration over a plug of silica gel eluting with dichloromethane to yield 1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone (18.2 g) as yellow solid. The compound is used without further purification.

Aufarbeitung

  1. customthe reaction is quenched with water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. filtrationThe crude product is purified by filtration over a plug of silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-47a109eae293408b818b08e6b8721a45
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383659B2

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