Diisopropylamine → 2-[(4-Methylphenyl)phenylmethylene]propanedinitrile
Reaction equation
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]=1Participants
Procedure
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).
Workup
- additionwas carefully added
- stirringthe resulting mixture was stirred for 30 min more
- temperatureit was heated
- temperatureat reflux for 2 days
- washthe resulting solution was washed with water
- extractionThe aqueous phase was extracted with ethyl acetate
- customthe combined organic phases were dried
- customthe solvent was removed
Sources & evidence
- ORD record
- ord-6b7e62966b354958bc2127abb0beea47
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05554624
Reaction notes
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