反応 #2705

反応方程式

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

溶媒

THF

ether

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 4 hours
2. 2
   洗浄washed with water (5 mL), brine (5 mL)
3. 3
   乾燥dried with MgSO4
4. 4
   その他Solvent was removed by distillation
5. 5
   その他The product was purified by silicagel chromatography

実験手順

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.

出典