Reacción #1985942

Ecuación de reacción

4-acetoxy-6-bromo-3-methoxybenzaldehyde

triethylamine

methyl acrylate

→

desired product

Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate

Disolventes

ether

water

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   LavadoThe organic layer is washed with water, brine
3. 3
   Secadodried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue is purified by HPLC
7. 7
   Lavadoeluting with 33% ethyl acetate in hexanes

Procedimiento

To a degassed solution of 4-acetoxy-6-bromo-3-methoxybenzaldehyde (15.4 g), and bis(triphenylphosphine)palladium (11) (1.2 g) in DMF (150 ml) is added triethylamine (31.9 ml) and methyl acrylate (19.6 g). The mixture is heated 135° C. for about 1.5 hours, cooled to room temperature and diluted with ether and water. The organic layer is washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by HPLC, eluting with 33% ethyl acetate in hexanes, then methylene chloride, to give the desired product.

Fuente