Реакция #43983

Уравнение реакции

2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde

3,5-dimethylaniline

acetic acid

sodium borohydride

→

N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amine

Выход 98.1%

Растворители

ethanol

toluene

Water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added to the solution
2. 2
   Другоеreacted at room temperature for 3 hrs
3. 3
   ДругоеThe organic layer was dried
4. 4
   Концентрированиеconcentrated
5. 5
   ДругоеThe obtained oily substance was purified by silica gel column chromatography

Методика

To a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde (15.0 mmol) in ethanol (44.6 mL) were added dropwise 3,5-dimethylaniline (15.8 mmol) and acetic acid (1.5 mmol) under a nitrogen atmosphere. The mixture was stirred at room temperature. After disappearance of the aldehyde was confirmed by gas chromatography, sodium borohydride (19.5 mmol) was added to the solution and reacted at room temperature for 3 hrs. Water and toluene were then added to the reaction mixture. The organic layer was dried and concentrated. The obtained oily substance was purified by silica gel column chromatography to give N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amine (4.88 g, yield 73.3%) as a yellow oily substance.

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