반응 #2701

반응 방정식

dry-ice

t-BuLi

pentane

1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene

Compound B

1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene

dimethylformamide

→

title compound

1-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

용매

ethylacetate

THF

반응 조건

후처리

1. 1
   세척washed with water (15 mL)
2. 2
   건조The organic layer was dried with MgSO4 and solvent
3. 3
   기타was removed under reduced pressure
4. 4
   기타The crude material was purified by silicagel chromatography

실험 절차

To a cold (-78° C.), stirred solution of 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound B 1 g, 3.2 mmol), in THF (17 mL) was added t-BuLi in pentane (1.7M solution, 3 mL, 5.1 mmol). After 10 minutes dry dimethylformamide (DMF) (600 mg, 8 mmol) was added and the dry-ice cooling was replaced with ice-water bath. The mixture was gradually warmed to ambient temperature and diluted with ethylacetate (150 mL), washed with water (15 mL). The organic layer was dried with MgSO4 and solvent was removed under reduced pressure. The crude material was purified by silicagel chromatography to afford the title compound as a white solid.

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