Reaction #470378

Reaction equation

Methylchloroformate

maleimide

NMM

→

product

Yield 55.0%

N-(Methoxycarbonyl)maleimide

Yield 55.0%

Solvents

EtOAc

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   Washwashed with EtOAc
3. 3
   Washwashed with cold water
4. 4
   Dryingdried over anhydrous Na2SO4
5. 5
   FiltrationAfter filtration and evaporation under vacuum a pink solid
6. 6
   Otherwas obtained
7. 7
   OtherPurification by column chromatography on silica gel (Hexane-EtOAc, 1:1

Procedure

Methylchloroformate (4.4 mL, 56.7 mmol, 1 eq) was added to a solution of maleimide (5.5 g, 56.7 mmol, 1 eq) and NMM (6.2 mL, 56.7 mmol, 1 eq) in 200 mL of EtOAc at 0° C. The suspension was stirred at 0° C. for 30 minutes, filtered and washed with EtOAc. Filtrate and washings were combined and washed with cold water and dried over anhydrous Na2SO4. After filtration and evaporation under vacuum a pink solid was obtained. Purification by column chromatography on silica gel (Hexane-EtOAc, 1:1, v/v) provided the product (4.8 g, 55%).

Source