Reaction #2701

Reaction equation

dry-ice

t-BuLi

pentane

1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene

Compound B

1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene

dimethylformamide

→

title compound

1-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

Solvents

ethylacetate

THF

Conditions

Workup

1. 1
   Washwashed with water (15 mL)
2. 2
   DryingThe organic layer was dried with MgSO4 and solvent
3. 3
   Otherwas removed under reduced pressure
4. 4
   OtherThe crude material was purified by silicagel chromatography

Procedure

To a cold (-78° C.), stirred solution of 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound B 1 g, 3.2 mmol), in THF (17 mL) was added t-BuLi in pentane (1.7M solution, 3 mL, 5.1 mmol). After 10 minutes dry dimethylformamide (DMF) (600 mg, 8 mmol) was added and the dry-ice cooling was replaced with ice-water bath. The mixture was gradually warmed to ambient temperature and diluted with ethylacetate (150 mL), washed with water (15 mL). The organic layer was dried with MgSO4 and solvent was removed under reduced pressure. The crude material was purified by silicagel chromatography to afford the title compound as a white solid.

Source