Hydrochloric Acid → 1-Phenylcyclopentanecarbonitrile

HRID 1409551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409551
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16]Br.Cl>CS(C)=O.O.CCOCC>[C:3]1([C:9]2([C:10]#[N:11])[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 80561,4-DibromobutaneHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

Produkt 1

HCID 661681-PhenylcyclopentanecarbonitrileAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a suspension of NaH (11.3 g, 281.7 mmol, 60%) in DMSO (75 ml) were added dropwise a mixture of phenyl-acetonitrile (15 g, 128.0 mmol) and 1,4-dibromo-butane (18 ml, 128.0 mmol) dissolved in DMSO:Ether (150 ml, 1:1) at 0° C. and the reaction mixture was stirred at room temperature (RT) for 2 to 3 h. After completion of the reaction, water and 10% HCl solution were added to the crude mass. It was extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated and purified by column chromatography (10% EtOAc-hexane) to get 1-phenyl-cyclopentanecarbonitrile (2) (19 g, 86.64%) as a yellow solid. MS: m/z=171 (MH+).

Aufarbeitung

  1. additionwere added dropwise
  2. additionwere added to the crude mass
  3. extractionIt was extracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography (10% EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b4203385e32e47fda13e193367799b70
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921388B2

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