反应详情

To a suspension of compound 361-A (9.21 g, 25.0 mmol) in DCM (50 mL), cooled in an ice-bath, was added an ice-cold solution of acetyl chloride (2.30 mL, 32.3 mmol), followed by SnCl4 (27.9 mmol) in DCM (200 mL). The reaction mixture was allowed to warm to ambient temperature and stirred for 18 h. The reaction mixture was quenched with saturated NH4Cl solution (125 mL), filtered over a pad of celite, dried over MgSO4, filtered and concentrated under vacuum. The residue was dissolved in refluxing EtOAc (75 mL), filtered hot and the filtrate allowed to cool. The solid was filtered and washed EtOAc (10 mL). Another batch of product was obtained by evaporation of the mother liquor, dissolving the residue in refluxing EtOAc (25 mL), filtering hot and allowing the filtrate to cool. The solid was filtered and washed with EtOAc (2 mL). The combined batches of solid were air-dried to afford 8.54 g of compound 361-B as a tan-orange powder. 1H-NMR (DMSO-d6) δ: 2.57 (s, 3H), 7.40-7.24 (m, 2H), 7.83-7.70 (m, 5H), 8.14 (d, 1H); MS: m/z 408.1 (M-H)−.

1. temperaturecooled in an ice-bath
2. customThe reaction mixture was quenched with saturated NH4Cl solution (125 mL)
3. filtrationfiltered over a pad of celite
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. dissolutionThe residue was dissolved
8. temperaturein refluxing EtOAc (75 mL)
9. filtrationfiltered hot
10. temperatureto cool
11. filtrationThe solid was filtered
12. washwashed EtOAc (10 mL)
13. customAnother batch of product was obtained by evaporation of the mother liquor
14. dissolutiondissolving the residue
15. filtrationfiltering hot
16. temperatureto cool
17. filtrationThe solid was filtered
18. washwashed with EtOAc (2 mL)
19. customThe combined batches of solid were air-dried