反应详情

A solution of ethyl 3,5-dihydroxyphenylacetate (4.0 g, 20.39 mmol), benzyl bromide (4.85 ml, 6.97 g, 40.77 mmol, 2 eq) and 5.64 g (40.77 mmol, 2 eq) of K2CO3 in 100 ml of acetone is refluxed overnight. The mixture is concentrated in vacuo, then partitioned between EtOAc and H2O. The organics are dried (MgSO4) and concentrated in vacuo. This is then passed through a flash silica gel column that is slurry packed with hexanes and eluted with 10% EtOAc in hexanes. Concentration of desired fractions gives ethyl 3,5-dibenzyloxyphenylacetate which is confirmed by NMR and used directly in the next step.

1. concentrationThe mixture is concentrated in vacuo
2. custompartitioned between EtOAc and H2O
3. dry with materialThe organics are dried (MgSO4)
4. concentrationconcentrated in vacuo
5. washeluted with 10% EtOAc in hexanes