反応 #2701

反応方程式

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

溶媒

ethylacetate

THF

反応条件

後処理

1. 1
   洗浄washed with water (15 mL)
2. 2
   乾燥The organic layer was dried with MgSO4 and solvent
3. 3
   その他was removed under reduced pressure
4. 4
   その他The crude material was purified by silicagel chromatography

実験手順

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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