Reaction #531804

Reaction equation

Acetic acid

4-pentynoic acid

N-hydroxy succinimide

DCC

→

10a

Yield 100.5%

Pent-4-ynoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Yield 100.5%

Solvents

THF

Conditions

Workup

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

Procedure

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).

Source