Reacción #2267084

ord-26a08a0a2db1494991c5a525adbb8539

Ecuación de reacción

CCCOC(=O)Cc1ccc(O)c(OC)c1
3-Methoxy-4-hydroxyphenylacetic acid propyl ester
CCCOC(=O)Cc1ccc(O)c(OC)c1
3-methoxy-4-hydroxyphenylacetic acid propyl ester
O=C([O-])[O-].[K+].[K+]
K2CO3
CCN(CC)C(=O)CCl
2-chloro-N,N-diethylacetamide
CCCOC(=O)Cc1ccc(OCC(=O)N(CC)CC)c(OC)c1
dark yellow oil
Rendimiento 95.0%
CCCOC(=O)Cc1ccc(OCC(=O)N(CC)CC)c(OC)c1
[4-[(N,N-diethylcarbamoyl)methoxy]-3-methoxyphenyl]acetic Acid Propyl Ester
Rendimiento 95.0%

Disolventes

Condiciones de reacción

Temperatura
60°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaUnder vigorous stirring, the suspension was warmed
  2. 2
    TemperaturaAfter cooling to room temperature the reaction mixture
  3. 3
    Filtraciónwas filtered
  4. 4
    Otrothe remaining solvent removed under reduced pressure

Procedimiento

3-Methoxy-4-hydroxyphenylacetic acid propyl ester (15-A) was dissolved in acetone. To the solution, 2 equivalents of K2CO3 were added, followed by 1.2 equivalent of 2-chloro-N,N-diethylacetamide. Under vigorous stirring, the suspension was warmed to reflux (60° C.) for ˜15 hours. After cooling to room temperature the reaction mixture was filtered and the remaining solvent removed under reduced pressure, giving a 95% yield of a dark yellow oil. The oily product was purified by silica column chromatography to produce the title compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06887866B2uspto-grants-2005_05