Reacción #2708

Ecuación de reacción

pTSA

3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone

Compound A

3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone

6-methyl-3-bromopyridine

n-BuLi

hexane

→

title compound

1-(6-Methyl-pyrid-3-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene

Disolventes

THF

ethyl acetate

ethyl acetate

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThis mixture was added to a flask
2. 2
   Otroat -78° C
3. 3
   workup.STIRRINGstirred for 16 hours
4. 4
   Lavadowashed with water (10 mL), brine (10 mL)
5. 5
   Secadodried with MgSO4
6. 6
   OtroSolvent was removed by distillation
7. 7
   workup.DISSOLUTIONthe crude material was dissolved in toluene (25 mL)
8. 8
   TemperaturaThe mixture was heated at 90° C. for 36 hours
9. 9
   Lavadowashed with 10% NaHCO3 (2×10 mL), brine (10 mL)
10. 10
    Secadodried with MgSO4
11. 11
    Otrothe solvent was removed by evaporation

Procedimiento

To a cold (-78° C.) solution of 6-methyl-3-bromopyridine (890 mg, 5.2 mmol) in THF (15 mL) was added n-BuLi in hexane (1.6M solution, 3.5 mL, 5.6 mmol) and stirred for 1 hour. This mixture was added to a flask containing 3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone (Compound A, 1.35 g, 5.4 mmol), in THF (5 mL) at -78° C. The reaction mixture was gradually warmed to ambient temperature and stirred for 16 hours. Thereafter it was diluted with ethyl acetate (100 mL), washed with water (10 mL), brine (10 mL) and dried with MgSO4. Solvent was removed by distillation, the crude material was dissolved in toluene (25 mL) and pTSA (530 mg, 2.8 mmol) was added. The mixture was heated at 90° C. for 36 hours. Thereafter it was diluted with ethyl acetate (100 mL), washed with 10% NaHCO3 (2×10 mL), brine (10 mL), dried with MgSO4 and the solvent was removed by evaporation. The title compound was obtained by recrystallization from ethyl acetate and hexane mixture (1:9).

Fuente