反应详情

Under N2 protection, triethylsilane (19.3 g, 166 mmol) and TFA (20 mL) were added successively to a mixture of 5-chloro-3-ethyl-3-hydroxy-2,3-dihydro-isoindol-1-one and 6-chloro-3-ethyl-3-hydroxy-2,3-dihydro-isoindol-1-one (3.52 g, 16.6 mmol). After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was treated with a satd. aq. solution of NaHCO3 (30 mL) and extracted with DCM (2×30 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude mixture of products. The desired regioisomer, 5-chloro-3-ethyl-2,3-dihydro-isoindol-1-one was obtained by prep-HPLC separation as a white solid (0.65 g, 20%). MS: 196.1 (M+H+).

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. additionThe residue was treated with a satd
3. extractionaq. solution of NaHCO3 (30 mL) and extracted with DCM (2×30 mL)
4. washThe combined organic layers were washed with brine
5. customdried over anhy
6. filtrationNa2SO4, filtered
7. concentrationconcentrated in vacuo
8. customto give a crude
9. additionmixture of products