反応 #2712

反応方程式

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

溶媒

ethyl acetate

THF

pentane

反応条件

後処理

1. 1
   workup.STIRRINGstirred for 3 hours
2. 2
   洗浄washed with brine (10 mL)
3. 3
   その他dried
4. 4
   その他the solvent was removed by evaporation
5. 5
   その他Purification by chromatography on silica gel column

実験手順

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.

出典