反应详情

To a solution of ethyl 3-(3,4-methylenedioxyphenyl)-1-oxoindene-2-carboxylate (100 mg, 0.31 mmol) in THF (2 ml) under an argon atmosphere at 0° C. was added a solution of freshly prepared 3-methoxyphenyl magnesium bromide (0.31 mmol). After stirring for 15 min, additional 3-methoxyphenyl magnesium bromide (0.06 mmol) was added. Stirring was continued for 45 min, at which time thin layer chromatographic analysis indicated that the reaction was incomplete. Additional 3-methoxyphenyl magnesium bromide (0.12 mmol) was added. After stirring for 2 h more, the mixture was partitioned between 3M HCl and EtOAc. The organic extract was washed successively with H2O, 5% aqueous NaHCO3, H2O and saturated aqueous NaCl. The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with 15% EtOAc/hexanes to afford the title compound (150 mg, 100%).

1. stirringStirring
2. waitwas continued for 45 min, at which time thin layer chromatographic analysis
3. stirringAfter stirring for 2 h more
4. customthe mixture was partitioned between 3M HCl and EtOAc
5. extractionThe organic extract
6. washwas washed successively with H2O, 5% aqueous NaHCO3, H2O and saturated aqueous NaCl
7. customThe solvent was removed in vacuo
8. customthe residue was purified by flash chromatography
9. washeluting with 15% EtOAc/hexanes