反应详情

温度

2.5 °C

NaH (0.32 g of a 60% dispersion in mineral oil, 8.0 mmol) was added to an ice-cold solution of 2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1.55 g, 6.7 mmol) in anhydrous DMF (30 mL). The mixture was purged with N2 and stirred at 0-5° C. for 45 minutes. Allyl iodide (0.91 mL, 10.0 mmol) was added and, after a few minutes, the cooling bath was removed and the mixture was stirred overnight at room temperature. Additional NaH (0.16 g of a 61.1% dispersion in mineral oil, 4.1 mmol) was added and the mixture was stirred at room temperature for 15 minutes. Allyl iodide (0.46 mL, 5.0 mmol) was added and the mixture was stirred at room temperature for 24 hours. The mixture was partitioned between EtOAc and water, and the aqueous phase was back-extracted with several portions of EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40M (4×15 cm) silica gel column, eluting with 1% to 4% EtOAc in hexane, to afford 2-allyl-2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone as an oil.

1. customThe mixture was purged with N2
2. customthe cooling bath was removed
3. stirringthe mixture was stirred overnight at room temperature
4. additionAdditional NaH (0.16 g of a 61.1% dispersion in mineral oil, 4.1 mmol) was added
5. stirringthe mixture was stirred at room temperature for 15 minutes
6. stirringthe mixture was stirred at room temperature for 24 hours
7. customThe mixture was partitioned between EtOAc and water
8. extractionthe aqueous phase was back-extracted with several portions of EtOAc
9. washThe combined organics were washed with brine
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated under vacuum
13. customThe residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40M (4×15 cm) silica gel column
14. washeluting with 1% to 4% EtOAc in hexane