Water → 3-Chloro-1-phenylpyrrolidin-2-one

HRID 271232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271232
[C:1]1([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.S([Cl:33])(C1C=CC(C)=CC=1)(=O)=O.O>C1COCC1.CCOC(C)=O>[Cl:33][CH:9]1[CH2:10][CH2:11][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]1=[O:12]

Komponenten

7

Edukt 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 783751-Phenylpyrrolidin-2-oneHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 219355593-Chloro-1-phenylpyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-Phenyl-2-pyrrolidinone (1 g, 6.2 mmol) in THF (60 mL, anhydrous) was cooled to −40° C. and LiHMDS (8 mL, 8 mmol, 1 M soln. in THF) was added. The resulting solution was stirred for 40 min. and tosyl chloride (1.78 g, 9.33 mmol) was then added. After warming the solution to RT over a 14 hour period, H2O added to quench reaction. The solution was then concentrated to provide an oil. Next, the oil was redissovled in EtOAc and washed with H2O and brine. The organic layer was dried over Na2SO4, filtered, and concentrated to an oil once again. Purified via flash column chromatography (4:1 hexane/EtOAc) provided 3-chloro-1-phenylpyrrolidin-2-one.

Aufarbeitung

  1. additionadded
  2. customto quench
  3. customreaction
  4. concentrationThe solution was then concentrated
  5. customto provide an oil
  6. washwashed with H2O and brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to an oil once again
  10. customPurified via flash column chromatography (4:1 hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-1690da9ee9d04d15a9e902f5e916c3ee
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452889B2

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