反応 #1477
ord-95296aadd2f34ea7a8a15d80c932bee0
反応方程式
反応物
試薬
溶媒
反応条件
後処理
- 1その他The reaction was quenched at 0° C. with saturated ammonium chloride solution (20 ml)
- 2抽出extracted with EtOAc (2×50 ml)
- 3抽出The combined extract
- 4洗浄was washed with water (20 ml), brine (20 ml)
- 5乾燥dried over MgSO4
- 6その他The solvent was evaporated under reduced pressure
- 7その他to afford a yellow oil
- 8その他The resultant reaction solution
- 9温度was heated in an oil bath (60° C.) for 3 h
- 10温度The reaction was cooled
- 11その他quenched with water (20 ml)
- 12抽出extracted with EtOAc (2×50 ml)
- 13抽出The combined extract
- 14洗浄was washed with saturated NaHCO3 (20 ml), water (20 ml), brine (20 ml)
- 15乾燥dried over MgSO4
- 16濃縮The solvent was concentrated in vacuo
実験手順
In a flame dried round bottom flask 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G, 2.0 g, 7.93 mmol) was dissolved in anhydrous THF (50 ml) and 3,4,5,6,-tetrahydro-2(H)-pyrimidinone (DMPU) (11.5 ml, 95.16 mmol) was added, under argon atmosphere. The reaction was then cooled to -20° C. and a solution of t-butyl magnesium chloride (16 ml, 31.7 mmol) (2M in Et2O) was added dropwise and stirred at -20° C. for 2 h and at ambient temperature for 1 h, under argon atmosphere. The reaction was quenched at 0° C. with saturated ammonium chloride solution (20 ml) and extracted with EtOAc (2×50 ml). The combined extract was washed with water (20 ml), brine (20 ml) and dried over MgSO4. The solvent was evaporated under reduced pressure to afford a yellow oil. To this yellow oil were added MeOH (50 ml) and p-tolylsulfonic acid (100 mg). The resultant reaction solution was heated in an oil bath (60° C.) for 3 h. The reaction was cooled and quenched with water (20 ml), extracted with EtOAc (2×50 ml). The combined extract was washed with saturated NaHCO3 (20 ml), water (20 ml), brine (20 ml), and dried over MgSO4. The solvent was concentrated in vacuo and the title compound was obtained as a colorless oil after purification by flash chromatography (silica, hexane).