Ethanol → 1-(Oct-7-enyl)-cyclopropene

Temperature

-78 °C

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.

1. customrecooled to −78° C
2. temperaturethe reaction mixture was warmed
3. temperatureto reflux for ½ hour
4. distillationto distill out of the reaction mixture
5. washThe reaction mixture was washed with water, 0.5M HCl (2×), water and brine
6. dry with materialIt was dried over MgSO4
7. filtrationfiltered
8. customThe product was purified by chromatography on silica gel

ORD record

ord-8c64df106f9d4203a153d539fb25673e

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06365549B2