反应详情

To a solution of N,N-dimethyl-m-phenylenediamine (120 mmol) in THF (500 mL) was added methyl bromoacetate (132 mmol) and DIPEA (264 mmol). The reaction mixture was refluxed for 16 h. Water (200 mL) and ethyl acetate (300 mL) were added, the layers were separated and the aqueous layer was extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with water (4×100 mL) and brine (100 mL) and dried over Na2SO4. The solvents were removed in vacuo and the residue was purified by flash-chromatography (ethyl acetate/heptane 1:4) to give 17.5 g (84.0 mmol, 70%) of an oily product which crystallized slowly.

1. temperatureThe reaction mixture was refluxed for 16 h
2. customthe layers were separated
3. extractionthe aqueous layer was extracted with ethyl acetate (2×200 mL)
4. washThe combined organic layers were washed with water (4×100 mL) and brine (100 mL)
5. dry with materialdried over Na2SO4
6. customThe solvents were removed in vacuo
7. customthe residue was purified by flash-chromatography (ethyl acetate/heptane 1:4)