Reaction #2705

Reaction equation

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

Solvents

THF

ether

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 4 hours
2. 2
   Washwashed with water (5 mL), brine (5 mL)
3. 3
   Dryingdried with MgSO4
4. 4
   OtherSolvent was removed by distillation
5. 5
   OtherThe product was purified by silicagel chromatography

Procedure

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.

Source