반응 #1477
ord-95296aadd2f34ea7a8a15d80c932bee0
반응 방정식
반응물
시약
용매
반응 조건
후처리
- 1기타The reaction was quenched at 0° C. with saturated ammonium chloride solution (20 ml)
- 2추출extracted with EtOAc (2×50 ml)
- 3추출The combined extract
- 4세척was washed with water (20 ml), brine (20 ml)
- 5건조dried over MgSO4
- 6기타The solvent was evaporated under reduced pressure
- 7기타to afford a yellow oil
- 8기타The resultant reaction solution
- 9온도was heated in an oil bath (60° C.) for 3 h
- 10온도The reaction was cooled
- 11기타quenched with water (20 ml)
- 12추출extracted with EtOAc (2×50 ml)
- 13추출The combined extract
- 14세척was washed with saturated NaHCO3 (20 ml), water (20 ml), brine (20 ml)
- 15건조dried over MgSO4
- 16농축The solvent was concentrated in vacuo
실험 절차
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).