Реакция #1483056

Уравнение реакции

(E)-cyclooct-4-enol

triethylamine

N,N-disuccinimidyl carbonate

→

title compound

Выход 75.5%

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

Выход 75.5%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   Другое(approximately 48 hours)
2. 2
   ДругоеThe acetonitrile was removed by rotary evaporation
3. 3
   Промывкаwashed with 0.1M HCl
4. 4
   Сушкаdried with magnesium sulfate
5. 5
   ДругоеThe ether was evaporated
6. 6
   Другоеthe resulting oil was purified by column chromatography (1:1 Ethyl Acetate:Hexane)

Методика

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).

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