4-Bromobutyronitrile → 5-benzyl-3,4-dihydro-2H-pyrrole

HRID 1045700

Reaktionsgleichung

Reaktionsgleichung von HRID 1045700
Br[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[CH2:7]([Mg]Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1.C(OCC)C>[CH2:7]([C:2]1[CH2:3][CH2:4][CH2:5][N:6]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 214124-BromobutyronitrileHCID 178419663HCID 178419663, Verbindung

Produkt 1

HCID 2240185-benzyl-3,4-dihydro-2H-pyrroleAusbeute 132,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 4-bromobutyronitrile (2.0 g, 13.5 mmol) in toluene (70 ml) was added 1.0 M benzylmagnesium bromide (20.0 ml, 20.0 mmol) in diethyl ether (70 ml) and the mixture was stirred for 2 hours at room temperature. The mixture was partitioned between 0.1N hydrochloric acid and ethyl acetate, and the organic layer was washed with aqueous sodium hydrogen carbonate, dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford 5-benzyl-3,4-dihydro-2H-pyrrole (2.85 g). This compound was used without further purification.

Aufarbeitung

  1. customThe mixture was partitioned between 0.1N hydrochloric acid and ethyl acetate
  2. washthe organic layer was washed with aqueous sodium hydrogen carbonate
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9ed19ab4a3214edb8f98f66172edcdf8
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569294B2

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