Reacción #75563

Ecuación de reacción

n-butyllithium

HMPA

1-chloromethylnaphthalene

diisopropylamine

α-tolunitrile

→

2-(2-Naphthalen-1-yl-ethyl)-benzonitrile

Rendimiento 95.2%

crude product

Rendimiento 95.2%

Disolventes

—

hexanes

THF

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe solution was stirred at −78° C. for one additional hour
2. 2
   workup.STIRRINGAfter stirring for one additional hour at −78° C.
3. 3
   Otrothe reaction was quenched with water
4. 4
   Extracciónextracted with Et2O (diethyl ether) (2×30 mL)
5. 5
   LavadoThe organic layer was washed with aqueous 1 N HCl (30 mL), water (3×30 mL), brine (30 mL)
6. 6
   Secadodried (Na2SO4)
7. 7
   OtroThe solvent was evaporated

Procedimiento

A solution of 1.26 mL (911 mg, 9.00 mmol) of diisopropylamine in 50 mL of THF (tetrahydrofuran) was cooled to −78° C. under nitrogen and 5.6 mL (9.0 mmol) of n-butyllithium, 1.6 M in hexanes, was added via syringe. The mixture was stirred at −78° C. for 1 hour and a solution of 353 mg (3.00 mmol) of α-tolunitrile in 10 mL of THF was added. The solution was stirred at −78° C. for one additional hour and a solution of 1.57 mL (9.00 mmol) of HMPA and 583 mg (3.30 mmol) of 1-chloromethylnaphthalene in 10 mL of THF was added dropwise. After stirring for one additional hour at −78° C., the reaction was quenched with water and extracted with Et2O (diethyl ether) (2×30 mL). The organic layer was washed with aqueous 1 N HCl (30 mL), water (3×30 mL), brine (30 mL) and dried (Na2SO4). The solvent was evaporated to give 735 mg of crude product which was used directly in the next step.

Fuente