Reaction #927261

Reaction equation

1,1,2-tribromo-2-pentyl-cyclopropane

n-butyllithium

tetramethylethylene diamine

1-bromo-2-pentene

→

1-pent-2-enyl-2-pentyl-cyclopropene

Yield 39.1%

Solvents

tetrahydrofuran

water

—

hexanes

Conditions

Workup

1. 1
   TemperatureTo this mixture, cooling in an ice water bath
2. 2
   workup.WAITfor three hours at room temperature
3. 3
   ExtractionThis residue was extracted with diethyl ether
4. 4
   OtherThe resulting mixture was transferred to a separatory funnel
5. 5
   Otherthe phases were separated
6. 6
   DryingThe organic layer was dried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   OtherThe solvent was removed from the filtrate in vacuo

Procedure

A solution of 1.00 g (0.00287 mol) of 1,1,2-tribromo-2-pentyl-cyclopropane in 4 ml of tetrahydrofuran was placed under an inert atmosphere of nitrogen via a Firestone valve. To this mixture, cooling in an ice water bath, was added via syringe 3.58 ml (0.00861 mol) of 1.6M n-butyllithium in hexanes. After 30 minutes, 0.432 ml (0.00287 mol) of tetramethylethylene diamine and 0.339 ml (0.00287 mol) of 1-bromo-2-pentene were added by syringe. The reaction stirred for one hour while warming to room temperature, then for three hours at room temperature. To the resulting mixture was added 2 ml of water. This residue was extracted with diethyl ether. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo to yield 0.200 g (39.1% of theory) of 1-pent-2-enyl-2-pentyl-cyclopropene as an oil.

Source