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

Temperatur

-78 °C

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.

1. stirringThe solution was stirred at −78° C. for one additional hour
2. stirringAfter stirring for one additional hour at −78° C.
3. customthe reaction was quenched with water
4. extractionextracted with Et2O (diethyl ether) (2×30 mL)
5. washThe organic layer was washed with aqueous 1 N HCl (30 mL), water (3×30 mL), brine (30 mL)
6. dry with materialdried (Na2SO4)
7. customThe solvent was evaporated

ORD-Eintrag

ord-9c7ed4ccb9c14cad9722ecb9ef5b342f

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06699873B1