반응 #531804

ord-16c9bb3b940c42ca96f547030d38d13f

반응 방정식

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
수율 100.5%
C#CCCC(=O)ON1C(=O)CCC1=O
Pent-4-ynoic acid 2,5-dioxo-pyrrolidin-1-yl ester
수율 100.5%

용매

반응 조건

온도
-10°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  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
    기타The resulting DCU was removed by filtration
  5. 5
    기타The filtrate was then evaporated

실험 절차

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).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08475768B2uspto-grants-2013_07