反応 #2700
ord-98343e58e325465bbbaa7fdb2b6a1ac0
反応方程式
反応物
試薬
反応条件
後処理
- 1温度heated to 70° C. for 30 minutes
- 2温度After cooling to ambient temperature
- 3温度heated to 70° C. for 24 hours
- 4温度The mixture was cooled to ambient temperature
- 5その他the reaction was quenched by addition of H2O
- 6workup.ADDITIONThe mixture was diluted with ether:ethylacetate (1:1, 100 mL)
- 7洗浄washed with saturated NH4Cl (15 mL), water (10 mL) and brine (10 mL)
- 8乾燥The organic layer was dried with MgSO4
- 9その他Solvent was removed under reduced pressure
- 10その他to afford the crude product as an off
- 11温度the mixture was refluxed for 16 hours
- 12温度The mixture was cooled to ambient temperature
- 13洗浄washed with 10% NaHCO3 (20 mL), brine (20 mL)
- 14乾燥dried with MgSO4
- 15その他the solvent wasremoved by evaporation
- 16その他Purification by chromatography on silica gel
実験手順
To a mixture of Mg metal (650 mg, 27 mmol) in THF (20 mL) was added 4-bromotoluene (5.3 g, 31 mmol) in THF (40 mL). The mixture was stirred for 2 hours at ambient temperature and heated to 70° C. for 30 minutes. After cooling to ambient temperature, 3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone (Compound A) (2.1 g, 8 mmol), in THF (5 mL) was added and heated to 70° C. for 24 hours. The mixture was cooled to ambient temperature and the reaction was quenched by addition of H2O. The mixture was diluted with ether:ethylacetate (1:1, 100 mL) and washed with saturated NH4Cl (15 mL), water (10 mL) and brine (10 mL). The organic layer was dried with MgSO4. Solvent was removed under reduced pressure to afford the crude product as an off. The product was dissolved in THF (20 mL). To this solution p-toleune sulfonic acid (pTSA) (35 mg) was added and the mixture was refluxed for 16 hours. The mixture was cooled to ambient temperature, diluted with ethylacetate (160 mL), washed with 10% NaHCO3 (20 mL), brine (20 mL), dried with MgSO4 and the solvent wasremoved by evaporation. Purification by chromatography on silica gel gave the title compound as a white solid.