Reacción #63023

Ecuación de reacción

3-Bromoquinoline

n-Butyllithium

N-(Dimethoxyacetyl)morpholine

→

title product

3-(Dimethoxyacetyl)quinoline

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 1.75 hours at the same temperature
3. 3
   OtroThe reaction was then quenched into 300 ml
4. 4
   OtroThe aqueous layer was separated
5. 5
   Extracciónextracted 4×100 ml
6. 6
   Secadodried over MgSO4

Procedimiento

3-Bromoquinoline (3.29 ml., 0.032 mol) was dissolved in 300 ml. THF and cooled to -78°. n-Butyllithium (13.6 ml. of 2.5M in hexane, 0.034 ml.) was added slowly and the mixture stirred 15 minutes at -75° to -78°. N-(Dimethoxyacetyl)morpholine (5.98 g., 0.032 mol) in 10 ml. THF was then added and stirring continued for 1.75 hours at the same temperature. The reaction was then quenched into 300 ml. saturated NH4Cl. The aqueous layer was separated and extracted 4×100 ml. ether. The organic layers were combined, dried over MgSO4, stripped to yield title product, 7.0 g., bp 120°-123°/0.125 torr.

Fuente