Cesium fluoride → 1-[4-(4-Chlorophenoxy)phenyl]-5-phenylpyrrolidin-2-one

HRID 1972235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972235
[F-].[Cs+].[C:3]1([CH:9]2[NH:13][C:12](=[O:14])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[C:16]1[CH:29]=[CH:28][C:19]([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:18][CH:17]=1>[Cu](I)I.CNCCNC.C(OCC)(=O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:19]2[CH:28]=[CH:29][C:16]([N:13]3[CH:9]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:10][CH2:11][C:12]3=[O:14])=[CH:17][CH:18]=2)=[CH:22][CH:23]=1

Komponenten

7

Edukt 3

HCID 25953Cesium fluoride2×HCID 956722-Pyrrolidinone, 5-phenyl-HCID 193519901-Chloro-4-(4-iodophenoxy)benzene

Produkt 1

HCID 569565971-[4-(4-Chlorophenoxy)phenyl]-5-phenylpyrrolidin-2-oneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8070N,N'-DimethylethylenediamineKatalysatorHCID 83717Copper iodideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Step A (Method 2, Using CsF as Base): To a 10 mL reaction tube fitted with a screw cap is charged with 5-phenylpyrrolidin-2-one (80.5 mg, 0.5 mmol), 1-(4-iodophenoxy)-4-chlorobenzene (248 mg, 0.75 mmol, 1.5 eq), copper iodide (5.0 mg, 0.025 mmol, 0.05 eq), CsF (189 mg, 1.25 mmol, 2.5 eq), N1,N2-dimethylethane-1,2-diamine (5.5 μL, 0.05 mmol, 0.1 eq) and ethyl acetate (1 mL). The system is degassed with argon then sealed and heated to 85° C. for 20 h. The reaction is cooled to room temperature, filtered and concentrated in vacuo. Purification on silica gel (0-33% ethyl acetate in hexane) gives 1-[4-(4-chlorophenoxy)phenyl]-5-phenylpyrrolidin-2-one as a colorless oil (182 mg, 100%).

Aufarbeitung

  1. customfitted with a screw
  2. customcap
  3. customThe system is degassed with argon
  4. customthen sealed
  5. temperatureThe reaction is cooled to room temperature
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification on silica gel (0-33% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0d1ff09e719445b38301b59a9d0d7147
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431607B2

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