Guaiacol → 1-Pyrrolidinecarboxylic acid, 2-oxo-, 2-methoxyphenyl ester

HRID 847219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 847219
[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].N1C=CC=CC=1.C[Si](C)(C)[N:22]1[CH2:26][CH2:25][CH2:24][C:23]1=[O:27]>C1C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:23]([N:22]1[CH2:26][CH2:25][CH2:24][C:1]1=[O:2])=[O:27]

Komponenten

6

Edukt 4

HCID 460GuaiacolHCID 1049PyridineHCID 6371PhosgeneHCID 844611-(Trimethylsilyl)pyrrolidin-2-one

Produkt 1

HCID 98160981-Pyrrolidinecarboxylic acid, 2-oxo-, 2-methoxyphenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel4×

Versuchsvorschrift

To a solution of phosgen (6.27 g, 63.3 mmol) in anhydrous benzene (30 ml) was dropwise added under ice-cooling a solution of 2-methoxyphenol (7.86 g, 63.3 mmol) and purified pyridine (5.00 g, 63.3 mmol) in anhydrous benzene (20 ml). The mixture was stirred overnight at room temperature. From a reaction solution were separated white precipitates by filtration, and a filtrate was evaporated under reduced pressure to give a colorless oily material. The oily material was dissolved in anhydrous benzene (20 ml), to which was added a solution of 1-trimethylsilyl-2-pyrrolidinone (9.66 g, 63.3 mmol) in anhydrous benzene (10 ml). The mixture was stirred at room temperature for 30 min. The reaction mixture was evaporated under reduced pressure to dryness to give a solid material. The desired product was separated using column chromatography on silica gel (eluted with benzene-acetone 20:1→1:1).

Aufarbeitung

  1. customFrom a reaction solution were separated white
  2. customprecipitates by filtration
  3. customa filtrate was evaporated under reduced pressure
  4. customto give a colorless oily material
  5. stirringThe mixture was stirred at room temperature for 30 min
  6. customThe reaction mixture was evaporated under reduced pressure to dryness
  7. customto give a solid material
  8. customThe desired product was separated

Quellen und Nachweise

ORD-Eintrag
ord-34a046a3a8834c87ae5213a3f7b562c3
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05140041

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