Réaction #1483056

Équation de réaction

(E)-cyclooct-4-enol

triethylamine

N,N-disuccinimidyl carbonate

→

title compound

Rendement 75.5%

(E)-cyclooct-4-enyl 2,5-dioxopyrrolidin-1-yl carbonate

Rendement 75.5%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Autre(approximately 48 hours)
2. 2
   AutreThe acetonitrile was removed by rotary evaporation
3. 3
   Lavagewashed with 0.1M HCl
4. 4
   Séchagedried with magnesium sulfate
5. 5
   AutreThe ether was evaporated
6. 6
   Autrethe resulting oil was purified by column chromatography (1:1 Ethyl Acetate:Hexane)

Mode opératoire

50 mg of (E)-cyclooct-4-enol (major isomer) and 0.2 mL triethylamine were added to 3 mL anhydrous acetonitrile. To this solution was slowly added 250 mg of N,N-disuccinimidyl carbonate. The reaction mixture was stirred at room temperature until thin layer chromatography revealed that the reaction was complete (approximately 48 hours). The acetonitrile was removed by rotary evaporation and the remaining residue was suspended in ether, washed with 0.1M HCl followed by brine, and dried with magnesium sulfate. The ether was evaporated and the resulting oil was purified by column chromatography (1:1 Ethyl Acetate:Hexane) yielding 80 mg (75% yield) of the title compound. 1H NMR (400 MHz CDCl3): δ 5.65-5.54 (m, 1H), 5.5-5.4 (m, 1H), 4.5-4.4 (m, 1H), 2.88-2.78 (s, 4H), 2.45-2.3 (m, 2H), 2.2-1.5 (m, 8H).

Source