Diisopropylamine → 2-[(4-Methylphenyl)phenylmethylene]propanedinitrile

HRID 742326노트

반응식

HRID 742326 반응식
C(NC(C)C)(C)C.[Li]CCCC.[C:13](#[N:17])[CH2:14][C:15]#[N:16].[CH3:18][C:19]1[CH:32]=[CH:31][C:22]([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=O)=[CH:21][CH:20]=1>O1CCCC1.C(OCC)(=O)C>[CH3:18][C:19]1[CH:32]=[CH:31][C:22]([C:23](=[C:14]([C:13]#[N:17])[C:15]#[N:16])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 8010MalononitrileHCID 86524-MethylbenzophenoneHCID 178418339Butyllithium

생성물 1

HCID 112650562-[(4-Methylphenyl)phenylmethylene]propanedinitrile수율 104.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 0.85 mL (6 mmol) of diisopropylamine in 11.3 mL of dry tetrahydrofuran, cooled to -78° C., was added 3.5 mL (5.6 mmol) of BuLi and the resulting mixture was stirred for 10 min. Next, 0.34 g (5.1 mmol) of malononitrile dissolved in 1.7 mL of tetrahydrofuran was carefully added and the resulting mixture was stirred for 30 min more. Finally, 1 g (5.1 mmol) of 4-methylbenzophenone in 1.7 mL of tetrahydrofuran was added. The mixture was allowed to warm up to room temperature and then it was heated at reflux for 2 days. Ethyl acetate was added and the resulting solution was washed with water. The aqueous phase was extracted with ethyl acetate and the combined organic phases were dried and the solvent was removed to yield 1.3 g of the desired product as a reddish oil (yield: quantitative).

후처리

  1. additionwas carefully added
  2. stirringthe resulting mixture was stirred for 30 min more
  3. temperatureit was heated
  4. temperatureat reflux for 2 days
  5. washthe resulting solution was washed with water
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. customthe combined organic phases were dried
  8. customthe solvent was removed

출처 및 근거

ORD 기록
ord-6b7e62966b354958bc2127abb0beea47
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05554624

반응 노트

불러오는 중…