Propargyl alcohol → 3-(2-Thienyl)-2-propyn-1-ol

HRID 2085354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085354
I[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([OH:10])[C:8]#[CH:9]>C(NC(C)C)(C)C.[Cu]I>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:9]#[C:8][CH2:7][OH:10]

Komponenten

5

Edukt 2

HCID 7859Propargyl alcoholHCID 189212-Iodothiophene

Produkt 1

HCID 110407693-(2-Thienyl)-2-propyn-1-olAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 7912DiisopropylamineLösungsmittel2×

Versuchsvorschrift

To a suspension of tetrakis (triphenylphosphine)palladium (300 mg, 0.25 mmol) and copper (I) iodide (100 mg, 0.50 mmol) in diisopropylamine (100 ml) under nitrogen was added 2-iodothiophene (6.3 g, 30 mmol). After stirring 1.5 h at room temperature a solution of propargyl alcohol (3.0 g, 33 mmol) in diisopropylamine (50 ml) was added. After 16 h at room temperature the mixture was filtered and concentrated in vacuo. The residue was submitted to flash chromatography using dichloromethane as eluent to give 3.0 g (73%) of 3-(2-thienyl)-2-propyn-1-ol as a crude product.

Aufarbeitung

  1. additionwas added
  2. filtrationAfter 16 h at room temperature the mixture was filtered
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-903dfb35432245a0b326ec54fd60de84
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720342B2

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