Reaction #927263

Reaction equation

ethanol

cyclopropene

sodium amide

8-Iodooct-1-ene

→

1-(oct-7-enyl)-cyclopropene

Yield 67.0%

Solvents

ammonia

ammonia

Ether

ammonia

ammonia

Conditions

Workup

1. 1
   Otherrecooled to −78° C
2. 2
   Temperaturethe reaction mixture was warmed
3. 3
   Temperatureto reflux for ½ hour
4. 4
   workup.DISTILLATIONto distill out of the reaction mixture
5. 5
   WashThe reaction mixture was washed with water, 0.5M HCl (2×), water and brine
6. 6
   DryingIt was dried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   OtherThe product was purified by chromatography on silica gel

Procedure

A mixture of 0.43 g (11 mmol) of sodium amide in roughly 15 ml of ammonia was cooled to −78° C. A chilled solution of cyclopropene in ammonia (1:1, 0.85 g, 10 mmol) was poured into the reaction mixture. The reaction mixture was stirred at −78° C. for ½ hour, warmed briefly to the ammonia boiling point, then recooled to −78° C. 8-Iodooct-1-ene (1.2 g, 5 mmol) was added by syringe, and the reaction mixture was warmed to reflux for ½ hour. A few ml of ethanol were added. Ether (25 ml) was slowly added while the ammonia was allowed to distill out of the reaction mixture. The reaction mixture was washed with water, 0.5M HCl (2×), water and brine. It was dried over MgSO4, filtered and stripped. The product was purified by chromatography on silica gel using hexane as the eluent. A 10 mg sample of 67% pure 1-(oct-7-enyl)-cyclopropene was obtained.

Source