Reaction #1483056

Reaction equation

(E)-cyclooct-4-enol

triethylamine

N,N-disuccinimidyl carbonate

→

title compound

Yield 75.5%

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

Yield 75.5%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Other(approximately 48 hours)
2. 2
   OtherThe acetonitrile was removed by rotary evaporation
3. 3
   Washwashed with 0.1M HCl
4. 4
   Dryingdried with magnesium sulfate
5. 5
   OtherThe ether was evaporated
6. 6
   Otherthe resulting oil was purified by column chromatography (1:1 Ethyl Acetate:Hexane)

Procedure

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