2-Iodoaniline → 2-(Hex-1-yn-1-yl)aniline

HRID 612438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612438
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].I[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10]>C(N(CC)CC)C.[Cu](I)I>[C:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 2

HCID 119952-IodoanilineHCID 127321-Hexyne

Produkt 1

HCID 107973102-(Hex-1-yn-1-yl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

32 mg of copper iodide and 140 mg of bistriphenyl phosphine palladium choride and 2.3 of 1-hexyne were added to a solution of 4.4 g of 2-iodo aniline in 100 ml of triethylamine and the mixture was stirred for 15 hours at ambient temperature, then evaporated to dryness. The residue was taken up in ether and the insoluble part was filtered out, wash with ether and the ethereal fractions were evaporated to dryness. The residue was chromatographed on silica (eluant: hexane-ethyl acetate (9-1)) to obtain 3.27 g of the desired product.

Aufarbeitung

  1. customevaporated to dryness
  2. filtrationthe insoluble part was filtered out
  3. washwash with ether
  4. customthe ethereal fractions were evaporated to dryness
  5. customThe residue was chromatographed on silica (eluant: hexane-ethyl acetate (9-1))

Quellen und Nachweise

ORD-Eintrag
ord-7dbfd8fe317d4580a65e0117eabea4e4
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06004979

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