تفاعل #927263

معادلة التفاعل

ethanol

cyclopropene

sodium amide

8-Iodooct-1-ene

→

1-(oct-7-enyl)-cyclopropene

المردود 67.0%

المذيبات

ammonia

ammonia

Ether

ammonia

ammonia

ظروف التفاعل

المعالجة

1. 1
   أخرىrecooled to −78° C
2. 2
   درجة الحرارةthe reaction mixture was warmed
3. 3
   درجة الحرارةto reflux for ½ hour
4. 4
   workup.DISTILLATIONto distill out of the reaction mixture
5. 5
   غسيلThe reaction mixture was washed with water, 0.5M HCl (2×), water and brine
6. 6
   تجفيفIt was dried over MgSO4
7. 7
   ترشيحfiltered
8. 8
   أخرىThe product was purified by chromatography on silica gel

الإجراء التجريبي

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.

المصدر