Phenylacetylene → 3-Phenyl-2-propynenitrile

HRID 1241595ノート

反応式

HRID 1241595 の反応式
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

参加物

5

反応物 3

HCID 10821PhenylacetyleneHCID 101761322-pyridyl cyanateHCID 178418339Butyllithium

生成物 1

HCID 963823-Phenyl-2-propynenitrile

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒3 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-41369278065140f2a187bf9fd1578d2e
出典データセット
uspto-grants-2006_10
特許番号
US07115617B2

反応ノート

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