반응 #1985946

반응 방정식

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

THF

triphenylphosphine

carbon tetrabromide

→

desired product

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

용매

ether

ether

반응 조건

후처리

1. 1
   여과filtered
2. 2
   농축The filtrate is concentrated in vacuo
3. 3
   여과the residue purified by filtration through silica gel in 50% ethyl acetate in hexanes
4. 4
   세척eluting with 25% ethyl acetate in hexanes

실험 절차

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.

출처