Reaktion #52856

Reaktionsgleichung

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched at 0° C. with saturated ammonium chloride solution (20 ml)
2. 2
   Extraktionextracted with EtOAc (2×50 ml)
3. 3
   ExtraktionThe combined extract
4. 4
   Waschenwas washed with water (20 ml), brine (20 ml)
5. 5
   Trocknendried over MgSO4
6. 6
   SonstigeThe solvent was evaporated under reduced pressure
7. 7
   Sonstigeto afford a yellow oil
8. 8
   SonstigeThe resultant reaction solution
9. 9
   Temperaturwas heated in an oil bath (60° C.) for 3 h
10. 10
    TemperaturThe reaction was cooled
11. 11
    Sonstigequenched with water (20 ml)
12. 12
    Extraktionextracted with EtOAc (2×(50 ml)
13. 13
    ExtraktionThe combined extract
14. 14
    Waschenwas washed with saturated NaHCO3 (20 ml), water (20 ml), brine (20 ml)
15. 15
    Trocknendried over MgSO4
16. 16
    EinengenThe solvent was concentrated in vacuo

Vorschrift

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).

Quelle