Réaction #43983

Équation de réaction

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

Rendement 98.1%

Solvants

ethanol

toluene

Water

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source