Triethylamine → Methyl 3-(4-nitrophenyl)propiolate

HRID 1910762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910762
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:18]([O:22][CH3:23])(=[O:21])[C:19]#[CH:20]>C1COCC1>[CH3:23][O:22][C:18](=[O:21])[C:19]#[C:20][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 124951-Iodo-4-nitrobenzeneHCID 13536Methyl propiolate

Produkt 1

HCID 251019Methyl 3-(4-nitrophenyl)propiolateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-Iodo-4-nitrobenzene (2.5 g, 10 mmol) was added to a solution of triethylamine (2.0 g, 20 mmol) in THF (40 mL). PdCl2 (PPh3)2 (0.14 g, 0.20 mmol), cuprous iodide (0.076 g, 0.40 mmol) and methyl propiolate (3.4 g, 40 mmol) were added and the resulting mixture was heated to reflux overnight. The reaction mixture was cooled to r.t., the solvent evaporated, and the crude compound dissolved in dichloromethane. The organics were filtered to remove insoluble material and the filtrate was washed with water, brine solution and dried over sodium sulfate. The filtrate was concentrated and the residue purified over silica gel using 15% ethyl acetate in petroleum ether as eluent to afford (4-nitrophenyl)-propynoic acid methyl ester (1.20 g, 59%) as a white solid.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux overnight
  3. customthe solvent evaporated
  4. dissolutionthe crude compound dissolved in dichloromethane
  5. filtrationThe organics were filtered
  6. customto remove insoluble material
  7. washthe filtrate was washed with water, brine solution
  8. dry with materialdried over sodium sulfate
  9. concentrationThe filtrate was concentrated
  10. customthe residue purified over silica gel using 15% ethyl acetate in petroleum ether as eluent

Quellen und Nachweise

ORD-Eintrag
ord-9347f1837b394c75a7048578f063a0cc
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604029B2

Notizen zur Reaktion

Wird geladen…