Реакция #531804

ord-16c9bb3b940c42ca96f547030d38d13f

Уравнение реакции

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

Реагенты

Нет

Растворители

Условия реакции

Температура
-10°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

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

Методика

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).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08475768B2uspto-grants-2013_07