Phenylacetylene → Propiolonitrile, phenyl-

HRID 1241595Notes

Reaction equation

HRID 1241595 reaction equation
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

Participants

5

Reactant 3

HCID 10821PhenylacetyleneHCID 101761322-pyridyl cyanateHCID 178418339Butyllithium

Product 1

HCID 96382Propiolonitrile, phenyl-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-41369278065140f2a187bf9fd1578d2e
Source dataset
uspto-grants-2006_10
Patent number
US07115617B2

Reaction notes

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