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

HRID 1110118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110118
[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, 140 mg of bistriphenyl phosphine palladium chloride and then 2.3 ml of 1-hexyne were added to a solution of 4.4 g of 2-iodo aniline in 100 ml of triethylamine. The mixture was stirred for 15 hours at ambient temperature, followed by evaporating to dryness and taking up in ether. The insoluble part was filtered off, washed 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. customby evaporating to dryness
  2. filtrationThe insoluble part was filtered off
  3. washwashed 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-cc4c0782514b4158a4812dae9b8defca
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05324839

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