反应 #1477
ord-95296aadd2f34ea7a8a15d80c932bee0
反应方程式
反应物
试剂
溶剂
反应条件
后处理
- 1其他The reaction was quenched at 0° C. with saturated ammonium chloride solution (20 ml)
- 2萃取extracted with EtOAc (2×50 ml)
- 3萃取The combined extract
- 4洗涤was washed with water (20 ml), brine (20 ml)
- 5干燥dried over MgSO4
- 6其他The solvent was evaporated under reduced pressure
- 7其他to afford a yellow oil
- 8其他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其他quenched with water (20 ml)
- 12萃取extracted with EtOAc (2×50 ml)
- 13萃取The combined extract
- 14洗涤was washed with saturated NaHCO3 (20 ml), water (20 ml), brine (20 ml)
- 15干燥dried over MgSO4
- 16浓缩The solvent was concentrated in vacuo
实验过程
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).