Reacción #1177

ord-33cc46ae4b86423a92b024e4bd6cb9eb

Ecuación de reacción

[Na]
sodium
CC(C)OC(C)C
isopropyl ether
COc1cccc(OC)c1C(C)=O
2,6-dimethoxyacetophenone
CCOC(=O)C(=O)[O-]
ethyl oxalate
C[O-].[Na+]
sodium methylate
→
COC(=O)C(=O)C=C([O-])c1c(OC)cccc1OC.[Na+]
expected product
COC(=O)C(=O)C=C([O-])c1c(OC)cccc1OC.[Na+]
Methyl 4-(2,6-dimethoxyphenyl)-4-oxido-2-oxo-3-butenoate sodium salt

Reactantes

[Na]
sodium
CC(C)OC(C)C
isopropyl ether
COc1cccc(OC)c1C(C)=O
2,6-dimethoxyacetophenone
CCOC(=O)C(=O)[O-]
ethyl oxalate
C[O-].[Na+]
sodium methylate

Reactivos

Ninguno

Disolventes

CO
MeOH
CO
MeOH

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe reaction mixture is heated
  2. 2
    Temperaturato reflux for 7 hours
  3. 3
    workup.WAITleft

Procedimiento

A solution of 100 g of 2,6-dimethoxyacetophenone and 7.5 ml of ethyl oxalate in 520 ml of anhydrous MeOH is added slowly to a solution of sodium methylate prepared from 12.7 g of sodium and 285 ml of anhydrous MeOH. The reaction mixture is heated to reflux for 7 hours and left overnight at RT. It is poured into 2 litres of isopropyl ether and left stirring for 15 minutes. The expected product is obtained by filtration, washing with isopropyl ether and drying under vacuum, m=120 g, m.p.=178° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723483uspto-grants-1998_03