Propargyl alcohol → 3-(4-Nitrophenyl)prop-2-yn-1-ol

HRID 24931

Reaktionsgleichung

Reaktionsgleichung von HRID 24931
[CH2:1]([OH:4])[C:2]#[CH:3].C(N(CC)CC)C.Br[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1>C(#N)C.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].[Cu]I>[OH:4][CH2:1][C:2]#[C:3][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1

Komponenten

8

Edukt 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 114661-Bromo-4-nitrobenzene

Produkt 1

HCID 50337133-(4-Nitrophenyl)prop-2-yn-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

8.55 g (0.15 mol) of propargyl alcohol and 152 ml (110 g, 1.09 mol) of triethylamine are added to a solution of 20.2 g (0.1 mol) of 4-bromonitrobenzene in 285 ml of acetonitrile. The reaction solution is heated to 100° C. 11.9 g (10 mmol) of Pd(Pph3)4 and 3.94 g (20 mmol) of copper (I) iodide are added. After 10 minutes the solvent is eliminated in vacuo and the residue taken up in ethyl acetate. It is washed with water and ammonia water, filtered through Celite and the solvent is eliminated in vacuo. The product is obtained by chromatography on silica gel (dichloromethane/methanol=10:1).

Aufarbeitung

  1. washIt is washed with water and ammonia water
  2. filtrationfiltered through Celite
  3. customThe product is obtained by chromatography on silica gel (dichloromethane/methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-7d8c42409bc3412a8e79172bc76b0462
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855710B2

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