تفاعل #52856

معادلة التفاعل

t-butyl magnesium chloride

MeOH

p-tolylsulfonic acid

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1-one

Compound G

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1-one

→

title compound

7-Bromo-1-(1,1-dimethylethyl)-3,4-dihydro-4,4-dimethylnaphthalene

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched at 0° C. with saturated ammonium chloride solution (20 ml)
2. 2
   استخلاصextracted with EtOAc (2×50 ml)
3. 3
   استخلاصThe combined extract
4. 4
   غسيلwas washed with water (20 ml), brine (20 ml)
5. 5
   تجفيفdried over MgSO4
6. 6
   أخرىThe solvent was evaporated under reduced pressure
7. 7
   أخرىto afford a yellow oil
8. 8
   أخرىThe resultant reaction solution
9. 9
   درجة الحرارةwas heated in an oil bath (60° C.) for 3 h
10. 10
    درجة الحرارةThe reaction was cooled
11. 11
    أخرىquenched with water (20 ml)
12. 12
    استخلاصextracted with EtOAc (2×(50 ml)
13. 13
    استخلاصThe combined extract
14. 14
    غسيلwas washed with saturated NaHCO3 (20 ml), water (20 ml), brine (20 ml)
15. 15
    تجفيفdried over MgSO4
16. 16
    تركيزThe solvent was concentrated in vacuo

الإجراء التجريبي

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) (2 M 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).

المصدر