반응 #2708

반응 방정식

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

용매

THF

ethyl acetate

ethyl acetate

THF

반응 조건

후처리

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

실험 절차

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).

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