Reacción #159760

Ecuación de reacción

5-bromo-2-chlorobenzaldehyde

6-bromo-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinoline

n-butyl lithium

→

(5-bromo-2-chloro-phenyl)-[1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinolin-6-yl]-methanol

Rendimiento 65.1%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for 30 min
2. 2
   Otroreaction
3. 3
   Otrowas quenched by the addition of saturated aqueous solution of ammonium chloride
4. 4
   Extracciónextracted with ethyl acetate (2×50 mL)
5. 5
   LavadoThe ethyl acetate layer was washed with water, brine
6. 6
   Secadodried over sodium sulphate
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe resulting residue was purified by silica gel column chromatography

Procedimiento

To a cooled solution of 6-bromo-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinoline (2.5 g, 7.5 mmol) in THF (30 mL) was added 1.6 M n-butyl lithium in hexanes (4.7 mL, 7.5 mmol) at −78° C., stirred for 30 min. This was transferred to a stirred solution of 5-bromo-2-chlorobenzaldehyde (1.73 g, 7.9 mmol) in THF (30 mL) at −78° C. After stirring for 30 min, reaction was quenched by the addition of saturated aqueous solution of ammonium chloride and extracted with ethyl acetate (2×50 mL). The ethyl acetate layer was washed with water, brine, dried over sodium sulphate, and concentrated. The resulting residue was purified by silica gel column chromatography to give (5-bromo-2-chloro-phenyl)-[1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinolin-6-yl]-methanol (2.31 g).

Fuente