Cesium carbonate → 1-(2-(4-Bromo-3,5-dimethylphenoxy)ethyl)pyrrolidin-2-one

HRID 237480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237480
C([O-])([O-])=O.[Cs+].[Cs+].CC1C=CC(S([O:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][C:21]2=[O:25])(=O)=O)=CC=1.[Br:26][C:27]1[C:32]([CH3:33])=[CH:31][C:30](O)=[CH:29][C:28]=1[CH3:35]>CN(C)C=O>[Br:26][C:27]1[C:32]([CH3:33])=[CH:31][C:30]([O:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][C:21]2=[O:25])=[CH:29][C:28]=1[CH3:35]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 447912072-(2-Oxopyrrolidin-1-yl)ethyl 4-methylbenzenesulfonate

Produkt 1

HCID 866971441-(2-(4-Bromo-3,5-dimethylphenoxy)ethyl)pyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Cs2CO3 (850 mg) is added to a solution of 2-(2-oxopyrrolidin-1-yl)ethyl 4-methylbenzenesulfonate (390 mg) and 4-bromo-3,5-dimethylphenol (200 mg) in N,N-dimethylformamide (4 mL). The mixture is heated to 50° C. for 12 hours and partitioned between diethylether and saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (ethyl acetate) to give the title compound. Yield: 210 mg; Mass spectrum (ESI+): m/z=312 [M+H]+.

Aufarbeitung

  1. custompartitioned between diethylether and saturated aqueous NH4Cl solution
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ab759291a5c144e28f17fe20b160ada6
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642585B2

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