反应详情

NaH (1.657 g, 60%, 41.4 mmol) was suspended in THF (10 mL). To this suspension was added malononitrile (1.368 g, 20.71 mmol) in THF (10 mL) at 0° C. dropwise over 10 minutes. The suspension was stirred for additional 20 minutes. To this solution was added compound 31A (5.11 g, 20.71 mmol) in THF (40 mL) portion wise. Afterwards, the solution was warmed to rt and stirred for 30 minutes. The pH of the solvent was adjusted to 1 with concentrated HCl. The reaction mixture was concentrated, and partitioned between water and EtOAc. The aqueous layer was extracted with additional EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was triturated with 1:1 Hex/EtOAc (50 mL) to give a solid which was collected by filtration to provide 3.7 g of the desired product 31B: 1H NMR (DMSO-d6): δ 7.60-7.63 (m, 2H), 7.32-7.47 (m, 5H), 7.03-7.07 (m, 2H), 5.16 (s, 2H). MS (DCI(+)): m/z 294 (M+NH4).

1. stirringstirred for 30 minutes
2. concentrationThe reaction mixture was concentrated
3. custompartitioned between water and EtOAc
4. extractionThe aqueous layer was extracted with additional EtOAc
5. washThe combined organic layers were washed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was triturated with 1:1 Hex/EtOAc (50 mL)
10. customto give a solid which
11. filtrationwas collected by filtration