Reaction #927243

Reaction equation

1,1,2-tribromo-2-hexyl-cyclopropane

methyl lithium

water

→

1-hexyl-cyclopropene

Yield 87.0%

Solvents

diethyl ether

diethyl ether

Conditions

Workup

1. 1
   TemperatureWhile cooling in an ice water bath
2. 2
   OtherThe resulting mixture was transferred to a separatory funnel
3. 3
   Otherthe phases were separated
4. 4
   DryingThe organic layer was dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   OtherThe solvent was removed from the filtrate in vacuo with a bath temperature under 20° C.

Procedure

A solution of 1.01 g (0.00278 mol) of 1,1,2-tribromo-2-hexyl-cyclopropane in 4 ml of diethyl ether was placed under a nitrogen atmosphere via use of a Firestone valve. While cooling in an ice water bath, 6.3 ml (0.00835 mol) of 1.4M methyl lithium in diethyl ether was added slowly by syringe. After 15 minutes, 2 ml of water was added via syringe. 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 with a bath temperature under 20° C. to yield 0.300 g (87% of theoretical) of 1-hexyl-cyclopropene pure as an oil.

Source