Reacción #2705

Ecuación de reacción

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

Disolventes

THF

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 4 hours
2. 2
   Lavadowashed with water (5 mL), brine (5 mL)
3. 3
   Secadodried with MgSO4
4. 4
   OtroSolvent was removed by distillation
5. 5
   OtroThe product was purified by silicagel chromatography

Procedimiento

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.

Fuente