반응 #2705

반응 방정식

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

용매

THF

ether

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 4 hours
2. 2
   세척washed with water (5 mL), brine (5 mL)
3. 3
   건조dried with MgSO4
4. 4
   기타Solvent was removed by distillation
5. 5
   기타The product was purified by silicagel chromatography

실험 절차

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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