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

HRID 742326ノート

反応式

HRID 742326 の反応式
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

参加物

7

反応物 4

HCID 7912DiisopropylamineHCID 8010MalononitrileHCID 86524-MethylbenzophenoneHCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6b7e62966b354958bc2127abb0beea47
出典データセット
uspto-grants-1996_09
特許番号
US05554624

反応ノート

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