Reacción #470378

ord-f1acf67d1cd44f2980ceb3ef2322c62b

Ecuación de reacción

COC(=O)Cl
Methylchloroformate
O=C1C=CC(=O)N1
maleimide
CN1CCOCC1
NMM
COC(=O)N1C(=O)C=CC1=O
product
Rendimiento 55.0%
COC(=O)N1C(=O)C=CC1=O
N-(Methoxycarbonyl)maleimide
Rendimiento 55.0%

Reactivos

Ninguno

Disolventes

Condiciones de reacción

Temperatura
0°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónfiltered
  2. 2
    Lavadowashed with EtOAc
  3. 3
    Lavadowashed with cold water
  4. 4
    Secadodried over anhydrous Na2SO4
  5. 5
    FiltraciónAfter filtration and evaporation under vacuum a pink solid
  6. 6
    Otrowas obtained
  7. 7
    OtroPurification by column chromatography on silica gel (Hexane-EtOAc, 1:1

Procedimiento

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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08367065B2uspto-grants-2013_02