Reaktion #217112

Reaktionsgleichung

water

Butyllithium

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

trimethyltin chloride

→

desired product

Ausbeute 152.2%

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

Ausbeute 152.2%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with methylene chloride
2. 2
   TrocknenThe extract was dried (Na2SO4)
3. 3
   Einengenconcentrated
4. 4
   Sonstigeto give the crude product
5. 5
   SonstigePurification by chromatography

Vorschrift

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.

Quelle