Reacción #1985946

Ecuación de reacción

methyl 5-hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

THF

triphenylphosphine

carbon tetrabromide

→

desired product

Methyl 5-Acetoxy-2-bromomethyl-4-methoxyhydrocinnamate

Disolventes

ether

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónfiltered
2. 2
   ConcentraciónThe filtrate is concentrated in vacuo
3. 3
   Filtraciónthe residue purified by filtration through silica gel in 50% ethyl acetate in hexanes
4. 4
   Lavadoeluting with 25% ethyl acetate in hexanes

Procedimiento

To a solution of methyl 5-hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate (5.21 g) in carbon tetrabromide (12.35 g) in anhydrous ether (75 ml) and anhydrous THF (50 ml) is added portionwise triphenylphosphine (9.78 g) and the mixture stirred at room temperature for 60 minutes, diluted with ether, then filtered. The filtrate is concentrated in vacuo and the residue purified by filtration through silica gel in 50% ethyl acetate in hexanes followed by HPLC, eluting with 25% ethyl acetate in hexanes, to give the desired product.

Fuente