Réaction #927263

Équation de réaction

ethanol

cyclopropene

sodium amide

8-Iodooct-1-ene

→

1-(oct-7-enyl)-cyclopropene

Rendement 67.0%

Solvants

ammonia

ammonia

Ether

ammonia

ammonia

Conditions de réaction

Traitement

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

Mode opératoire

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