Reacción #2716

Ecuación de reacción

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

Disolventes

ethyl acetate

THF

pentane

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with brine (10 mL)
2. 2
   Otrodried
3. 3
   Otrothe solvent was removed by evaporation
4. 4
   OtroPurification by chromatography on silica gel column

Procedimiento

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.

Fuente