Phenylacetylene → 3-Phenyl-2-propynenitrile

HRID 1241595노트

반응식

HRID 1241595 반응식
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

참가 물질

5

반응물 3

HCID 10821PhenylacetyleneHCID 101761322-pyridyl cyanateHCID 178418339Butyllithium

생성물 1

HCID 963823-Phenyl-2-propynenitrile

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-41369278065140f2a187bf9fd1578d2e
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115617B2

반응 노트

불러오는 중…