Reacción #217112

Ecuación de reacción

water

Butyllithium

8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene

trimethyltin chloride

→

desired product

Rendimiento 152.2%

2-Di-n-propylamino-8-trimethylstannyl-1,2,3,4-tetrahydronaphthalene

Rendimiento 152.2%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with methylene chloride
2. 2
   SecadoThe extract was dried (Na2SO4)
3. 3
   Concentraciónconcentrated
4. 4
   Otroto give the crude product
5. 5
   OtroPurification by chromatography

Procedimiento

Butyllithium (1.2M in hexane; 2.8 ml; 3.4 mmol) was added to a solution of 8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene (1 g; 3.22 mmol) in THF (50 ml) at -78° C. After 1.5 hr., a solution of trimethyltin chloride (1.3 g, 2.0 mmol) in THF (20 ml) was added. The reaction mixture was allowed to warm to room temperature, stirred overnight at room temperature, poured into water, and extracted with methylene chloride. The extract was dried (Na2SO4) and concentrated to give the crude product. Purification by chromatography using 1:10 methanol:methylene chloride gave 1.2 g of the desired product which was used directly in the next step.

Fuente