反应 #531804

ord-16c9bb3b940c42ca96f547030d38d13f

反应方程式

CC(=O)O
Acetic acid
C#CCCC(=O)O
4-pentynoic acid
O=C1CCC(=O)N1O
N-hydroxy succinimide
C(=NC1CCCCC1)=NC1CCCCC1
DCC
C#CCCC(=O)ON1C(=O)CCC1=O
10a
收率 100.5%
C#CCCC(=O)ON1C(=O)CCC1=O
Pent-4-ynoic acid 2,5-dioxo-pyrrolidin-1-yl ester
收率 100.5%

溶剂

反应条件

温度
-10°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.WAITthen left
  2. 2
    workup.STIRRINGto stir at room temperature overnight
  3. 3
    workup.WAIT(A white precipitate was observed after 15 min
  4. 4
    其他The resulting DCU was removed by filtration
  5. 5
    其他The filtrate was then evaporated

实验过程

4-pentynoic acid (5.0 g, 51 mmol) and N-hydroxy succinimide (5.87 g, 51 mmol) were added to a solution of DCC (12.6 g, 61.2 mmol) in THF (125 ml) at −10° C. The mixture was then stirred for 1 h at −10° C. then left to stir at room temperature overnight. (A white precipitate was observed after 15 min). Acetic acid (0.63 ml) was then added. The resulting DCU was removed by filtration. The filtrate was then evaporated to give 10a (10 g, 100% crude yield).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08475768B2uspto-grants-2013_07