反应详情

To a 100 mL round bottomed flask equipped with a magnetic stir bar, rubber septum, and argon inlet containing DMF (25 mL) in an ice bath was placed 1 (17.5 g, 76.1 mmol) and the reaction was stirred at rt until the solid dissolved. To this solution was added N,N-dimethylformamide dimethyl acetal (60 g) and the mixture was heated at 40° C. for 4 h. Solvent was removed in vacuo at 42° C. and the residue was dissolved in anhydrous DMF (60 mL). To this solution at 0° C. was added portion wise NaH (4.56 g, 60% in oil, 114 mmol) and the reaction was stirred at 0° C. for 30 min. To this mixture was added propargyl bromide (18 g, 80% toluene solution, 121.7 mmol) dropwise. Ice bath was removed and the mixture was stirred at rt for 1 h. The residue was poured into a mixture of water and EtOAc (200 mL/200 mL). The mixture was filtered and solid was collected and dissolved in DCM (300 mL) and washed with saturated NaHCO3 (3×200 mL) and water (200 mL). To this solution was added 100 g of silica gel and dried in vacuo. The solid mixture was loaded on silica gel column and eluted with 10% EtOAc in DCM to afford compound 2 as a yellow solid (9.2 g, 37.4%).

1. customTo a 100 mL round bottomed flask equipped with a magnetic stir bar
2. dissolutiondissolved
3. temperaturethe mixture was heated at 40° C. for 4 h
4. customSolvent was removed in vacuo at 42° C.
5. dissolutionthe residue was dissolved in anhydrous DMF (60 mL)
6. stirringthe reaction was stirred at 0° C. for 30 min
7. customIce bath was removed
8. stirringthe mixture was stirred at rt for 1 h
9. additionThe residue was poured into a mixture of water and EtOAc (200 mL/200 mL)
10. filtrationThe mixture was filtered
11. customsolid was collected
12. dissolutiondissolved in DCM (300 mL)
13. washwashed with saturated NaHCO3 (3×200 mL) and water (200 mL)
14. additionTo this solution was added 100 g of silica gel
15. customdried in vacuo
16. washeluted with 10% EtOAc in DCM