Reacción #89788

Ecuación de reacción

chloride

4-acetoxyconiferyl alcohol

4-acetoxyferuloyl chloride

Et3N

4-acetoxyconiferyl alcohol

→

diacetate

coniferyl ferulate

Rendimiento 94.0%

Disolventes

CHCl3 EtOAc

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   Lavadowashed successively with aqueous 3% HCl and saturated NH4Cl
3. 3
   SecadoDrying over MgSO4, evaporation, and purification by flash chromatography [CHCl3/EtOAc (19:1)]

Procedimiento

Coupling of 4-acetoxyferuloyloyl chloride with 4-acetoxyconiferyl alcohol was efficiently carried out using 4-(dimethylamino)-pyridine (DMAP). Thus, 4-acetoxyconiferyl alcohol and 4-acetoxyferuloyl chloride were dissolved in dry CH2Cl2 (120 mL) to which DMAP (0.25 equiv) and Et3N (0.85 equiv) were added. The mixture was stiffed for 2 h, when TLC [CHCl3/EtOAc (5:1)] showed the starting material was converted into a faster moving compound. The solution was diluted with CH2Cl2 and washed successively with aqueous 3% HCl and saturated NH4Cl. Drying over MgSO4, evaporation, and purification by flash chromatography [CHCl3/EtOAc (19:1)] gave the diacetate of coniferyl ferulate (94%) as a pale yellow oil.

Fuente