1-Pentyne → Methyl 3-nitro-4-(1-pentynyl)benzoate

HRID 1780817

Reaktionsgleichung

Reaktionsgleichung von HRID 1780817
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH:15]#[C:16][CH2:17][CH2:18][CH3:19]>C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:12]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[C:15]#[C:16][CH2:17][CH2:18][CH3:19])[C:6]([O:8][CH3:9])=[O:7])([O-:14])=[O:13]

Komponenten

5

Edukt 2

HCID 123091-PentyneHCID 735797Methyl 4-chloro-3-nitrobenzoate

Produkt 1

HCID 19047718Methyl 3-nitro-4-(1-pentynyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A solution of methyl 4-chloro-3-nitrobenzoate (0.70 g), bis(triphenylphosphine) palladium chloride (0.12 g), and 1-pentyne (2 mL) in triethylamine (12 mL) was placed in a sealed tube. The mixture was heated to 75° C. and stirred 18 h. The reaction mixture was cooled, filtered, and concentrated in vacuo. The resulting brown residue was chromatographed on silica gel with hexane/ethyl acetate 9/1 to obtain the product. NMR (300 MHz, CDCl3) δ 8.61 (1H, d, J=2 Hz), 8.16 (1H, m), 7.64 (1H, m), 3.96 (3H, s), 2.49 (2H, t, J=7 Hz), 1.66 (2H, m, J=7 Hz), 1.06 (3H, t, J=7 Hz).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting brown residue was chromatographed on silica gel with hexane/ethyl acetate 9/1
  5. customto obtain the product

Quellen und Nachweise

ORD-Eintrag
ord-67fb6a8da0f648e394c64e542a3e0633
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05631280

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