Reaktion #2716

Reaktionsgleichung

DMF

2,2-dimethyl-4(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene

Compound R

2,2-dimethyl-4(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene

t-BuLi

→

title compound

2,2-Dimethyl-4(5-methyl-thien-2-yl)-chrom-3-en-6-al

Lösungsmittel

ethyl acetate

THF

pentane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To a cold (-78° C.) solution of 2,2-dimethyl-4(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene (Compound R, 1.2 g, 3.6 mmol) in THF (10 mL), was added t-BuLi in pentane (1.7M solution, 2.3 mL). After 30 minutes, DMF (465 mg, 5 mmol) was added and the mixture was allowed to warm to ambient temperature and stirred for 3 hours. The mixture 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.

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