Реакция #2705

Уравнение реакции

1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene

Compound F

1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene

t-BuLi

pentane

dry-ice

DMF

→

title compound

1(5-Methyl-thien-2-yl) 3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

Растворители

THF

ether

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 4 hours
2. 2
   Промывкаwashed with water (5 mL), brine (5 mL)
3. 3
   Сушкаdried with MgSO4
4. 4
   ДругоеSolvent was removed by distillation
5. 5
   ДругоеThe product was purified by silicagel chromatography

Методика

To a cold (-78° C.) solution of 1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound F, 1.35 g, 4.1 mmol), in THF (20 mL) was added t-BuLi in pentane (1.7M solution, 3.5 mL, 5.95 mmol). The reaction was stirred for 15 minutes and DMF (600 mg, 5.8 mmol) was added and dry-ice cooling was replaced with ice-water bath. The mixture was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with ether (70 mL) and washed with water (5 mL), brine (5 mL) and dried with MgSO4. Solvent was removed by distillation. The product was purified by silicagel chromatography to afford the title compound as a colorless oil.

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