反応 #1483056

反応方程式

(E)-cyclooct-4-enol

triethylamine

N,N-disuccinimidyl carbonate

→

title compound

収率 75.5%

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

収率 75.5%

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他(approximately 48 hours)
2. 2
   その他The acetonitrile was removed by rotary evaporation
3. 3
   洗浄washed with 0.1M HCl
4. 4
   乾燥dried with magnesium sulfate
5. 5
   その他The ether was evaporated
6. 6
   その他the resulting oil was purified by column chromatography (1:1 Ethyl Acetate:Hexane)

実験手順

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).

出典