Réaction #46738

Équation de réaction

NaOH

4-amino-2-(2-methoxy-ethoxymethoxy)-benzonitrile

4-fluorobenzaldehyd

sodium triacetoxyborohydride

→

pure product

Rendement 70.6%

4-(4-Fluoro-benzylamino)-2-(2-methoxy-ethoxymethoxy)-benzonitrile

Rendement 70.6%

Solvants

1,2-dichloroethan

Conditions de réaction

Traitement

1. 1
   Autredried
2. 2
   Filtrationby filtering through a silicone
3. 3
   Filtrationfilter
4. 4
   Autreevaporated onto SiO2
5. 5
   Autrepurified by column chromatography (SiO2-heptane/EtOAc=2:1)

Mode opératoire

To a solution of 4-amino-2-(2-methoxy-ethoxymethoxy)-benzonitrile (666 mg; 3 mmol) in 1,2-dichloroethan (15 mL) was added 4-fluorobenzaldehyd (496 mmol; 4 mmol) and carefully sodium triacetoxyborohydride (933 mg; 4.4 mmol). The mixture was stirred at 60° C. for 6 hours. The reaction mixture was added 1 M NaOH (aq.), dried by filtering through a silicone filter, evaporated onto SiO2 and purified by column chromatography (SiO2-heptane/EtOAc=2:1) to yield 700 mg pure product.

Source