Reaktion #2712

Reaktionsgleichung

DMF

2,2-dimethyl-4(tol-4-yl)-6-bromo-chrom-3-ene

Compound P

2,2-dimethyl-4(tol-4-yl)-6-bromo-chrom-3-ene

t-BuLi

→

title compound

2,2-Dimethyl-4(tol-4-yl)-chrom-3-en-6-al

Lösungsmittel

ethyl acetate

THF

pentane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 3 hours
2. 2
   Waschenwashed with brine (10 mL)
3. 3
   Sonstigedried
4. 4
   Sonstigethe solvent was removed by evaporation
5. 5
   SonstigePurification by chromatography on silica gel column

Vorschrift

To a cold (-78° C.) solution of 2,2-dimethyl-4(tol-4-yl)-6-bromo-chrom-3-ene (Compound P, 480 mg, 1.45 mmol) in THF (10 mL), was added t-BuLi in pentane (1.7M solution, 1.1 mL) and the mixture was stirred for 30 minutes. DMF (200 mg, 2.9 mmol) was added, the mixture was warmed to ambient temperature and stirred for 3 hours. The reaction was diluted with ethyl acetate (150 mL), washed with brine (10 mL), dried and the solvent was removed by evaporation. Purification by chromatography on silica gel column gave the title compound as a colorless oil.

Quelle