反応 #1985946

反応方程式

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

THF

triphenylphosphine

carbon tetrabromide

→

desired product

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

溶媒

ether

ether

反応条件

後処理

1. 1
   ろ過filtered
2. 2
   濃縮The filtrate is concentrated in vacuo
3. 3
   ろ過the residue purified by filtration through silica gel in 50% ethyl acetate in hexanes
4. 4
   洗浄eluting with 25% ethyl acetate in hexanes

実験手順

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.

出典