Phenylacetylene → 3-Phenyl-2-propynenitrile

HRID 1241595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1241595
C([Li])CCC.[C:6]1([C:12]#[CH:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N:14]1C=CC=C[C:15]=1OC#N>CCOCC>[C:6]1([C:12]#[C:13][C:15]#[N:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 10821PhenylacetyleneHCID 101761322-pyridyl cyanateHCID 178418339Butyllithium

Produkt 1

HCID 963823-Phenyl-2-propynenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-Butyllithium (21.6 mL, 2.5M in hexane) was added dropwise to a solution of phenylacetylene (5 g, 0.05 mol) in dry Et2O (200 mL) maintaining at −78° C. under inert atmosphere. A solution of 2-pyridyl cyanate (7.2 g, 0.06 mol) in dry Et2O (100 mL) was added dropwise keeping the temperature below −60° C. The mixture was stirred for 30 min at −78° C. then warmed to RT. The reaction was diluted with Et2O and quenched with 1N NaOH. The organic layer was washed once with 1N HCl and once with saturated NaHCO3. The solvent was removed under vacuum maintaining the temperature under 30° C. to give 3-phenyl-2-propynenitrile as a colorless crystalline solid.

Aufarbeitung

  1. customthe temperature below −60° C
  2. temperaturethen warmed to RT
  3. customquenched with 1N NaOH
  4. washThe organic layer was washed once with 1N HCl and once with saturated NaHCO3
  5. customThe solvent was removed under vacuum
  6. temperaturemaintaining the temperature under 30° C.

Quellen und Nachweise

ORD-Eintrag
ord-41369278065140f2a187bf9fd1578d2e
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115617B2

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