تفاعل #531804

ord-16c9bb3b940c42ca96f547030d38d13f

معادلة التفاعل

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

الكواشف

لا شيء

المذيبات

ظروف التفاعل

درجة الحرارة
-10°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08475768B2uspto-grants-2013_07