反应详情

温度

90 °C

To a stirred solution of 5-bromo-7-isopropylindoline-2,3-dione (45.1 g, 0.17 mol) in THF (275 ml) at room temperature under a nitrogen atmosphere, was added, via syringe, 2.0 M solution of LiBH4/THF (215 ml) over 30 min. The reaction mixture was stirred at 90° C. for 1 hr, cooled, quenched with distilled water and 5% HCl, and extracted with EtOAc. The extracts were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude product was purified by elution from a silica gel column with hexane/EtOAc (9:1) to give (14.5 g, 36%) of the product. 1H NMR (300 MHz, CDCl3) δ 8.18 (b, NH), 7.62 (d, 1H), 7.21 (t, 1H), 7.16 (d, 1H), 6.51 (dd, 1H), 3.20 (m, 1H), 1.38 (d, 6H); ESI (+) MS m/e=239 (MH+), ESI (−) MS m/e=237 (MH−).

1. temperaturecooled
2. customquenched with distilled water and 5% HCl
3. extractionextracted with EtOAc
4. washThe extracts were washed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated under reduced pressure
7. customThe crude product was purified by elution from a silica gel column with hexane/EtOAc (9:1)