反応 #1265368

反応方程式

hexanoic acid

N-hydroxy succinimide

DCCI

→

N-hexanoyloxy succinimide

収率 74.3%

溶媒

DMF

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度The mixture was cooled with an ice-water bath
3. 3
   その他The dicyclohexyl urea (DCU) precipitate was removed by filtration
4. 4
   その他the DMF solvent was removed by vacuum rotary evaporation
5. 5
   洗浄The yellow oil residue was washed with water and hexane
6. 6
   その他to yield a white solid, which
7. 7
   その他dried at 78° C.

実験手順

To a solution of 4.64 g (0.04 mol) of hexanoic acid and 5.75 g (0.05 mol) of N-hydroxy succinimide in 100 mL distilled DMF, 10.3 g (0.05 mol) of DCCI was added. The mixture was cooled with an ice-water bath and stirred for 5 h. The dicyclohexyl urea (DCU) precipitate was removed by filtration, and the DMF solvent was removed by vacuum rotary evaporation. The yellow oil residue was washed with water and hexane to yield a white solid, which was vacuum dried at 78° C. to give 6.34 g (74%) of N-hexanoyloxy succinimide. IR (KBr): 1816 cm−1 (υ(C═O) of ester), 1745–1786 cm−1 (υ(C═O) of imide). 1H-NMR (DMSO-d6, ppm): 0.86 (3 H, —CH3), 1.31 (4H, —(CH2)2CH3), 1.62 (2H, —CH2CH2COO—), 2.64 (2H, —CH2COO—), 2.80 (4H, —COCH2CH2CO—).

出典