تفاعل #1483056

معادلة التفاعل

(E)-cyclooct-4-enol

triethylamine

N,N-disuccinimidyl carbonate

→

title compound

المردود 75.5%

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

المردود 75.5%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرى(approximately 48 hours)
2. 2
   أخرىThe acetonitrile was removed by rotary evaporation
3. 3
   غسيلwashed with 0.1M HCl
4. 4
   تجفيفdried with magnesium sulfate
5. 5
   أخرىThe ether was evaporated
6. 6
   أخرىthe resulting oil was purified by column chromatography (1:1 Ethyl Acetate:Hexane)

الإجراء التجريبي

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).

المصدر