Reaktion #2720

Reaktionsgleichung

DMF

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

Compound T

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

n-BuLi

→

title compound

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

Lösungsmittel

THF

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigerecooled to -78° C
2. 2
   SonstigeThe reaction was quenched
3. 3
   workup.ADDITIONby adding water (10 mL) and ethy lacetate (100 mL)
4. 4
   WaschenThe organic layer was washed with brine (10 mL)
5. 5
   Sonstigedried
6. 6
   Sonstigethe solvent was removed by distillation

Vorschrift

To a cold (-78° C.) solution of 2,2-dimethyl-4(2-methyl-thien-5-yl)-6-bromo-thiochrom-3-ene (Compound T, 430 mg, 1.2 mmol) in THF (12 mL) was added n-BuLi in hexane (1.6M solution, 1 mL). The mixture was gradually warmed to ambient temperature over 1 hour and recooled to -78° C. To this solution was added DMF (220 mg, 3 mmol) and the mixture was stirred at ambient temperature for 16 hours. The reaction was quenched by adding water (10 mL) and ethy lacetate (100 mL). The organic layer was washed with brine (10 mL), dried and the solvent was removed by distillation to obtain the title compound as a pale yellow oil.

Quelle