Sodium Iodide → HCID 54005299, Verbindung

HRID 2399996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2399996
[C:1](=O)([O-])[O-].[K+].[K+].[I-].[Na+].[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.BrC[CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([O:28][CH3:29])=[O:27]>C(#N)C.ClCCl>[N:9]1([CH2:1][CH:17]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH3:16])[CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 10589341HCID 10589341, Verbindung

Produkt 1

HCID 54005299HCID 54005299, VerbindungAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

18.4 g of potassium carbonate, 4.5 g of sodium iodide and then 9.54 g of pyrrolidine are successively added to a solution of 36 g of methyl 2-(3-bromopropoxy)phenyl-acetate in 400 cm3 of acetonitrile. The reaction mixture is refluxed for 5 hours and then stirred at 20° C. for 20 hours and diluted with 800 cm3 of dichloromethane. The solution is washed with 80 cm3 of water and then twice with 80 cm3 of brine. The chloromethylenic phase is dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 4.5 cm, height 48 cm), eluting under a nitrogen pressure of 0.4 bar with an ethyl acetate and methanol mixture (90/10 by volume) and collecting fractions of 500 cm3. Fractions 3 to 8 are pooled and concentrated to dryness at 50° C. under reduced pressure (2.7 kPa). 24.9 g of methyl {[3-(1-pyrrolidinyl)-2-propoxy]phenyl}acetate are obtained in the form of an orange-colored oil.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. washThe solution is washed with 80 cm3 of water
  3. dry with materialThe chloromethylenic phase is dried over sodium sulphate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 4.5 cm, height 48 cm)
  6. washeluting under a nitrogen pressure of 0.4 bar with an ethyl acetate and methanol mixture (90/10 by volume)
  7. customcollecting fractions of 500 cm3
  8. concentrationconcentrated to dryness at 50° C. under reduced pressure (2.7 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-95e622510e4b40eb86742edf9b26f4bf
Quelldatensatz
uspto-grants-1995_09
Patentnummer
US05451601

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