Reaktion #2711

Reaktionsgleichung

DMF

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

Compound N

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

n-BuLi

→

2,2-Dimethyl-4(tol-4-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), ethyl acetate (100 mL)
4. 4
   Waschenthe organic layer was washed with brine (10 mL)
5. 5
   Sonstigedried
6. 6
   Sonstigethe solvent removed by distillation
7. 7
   SonstigeThe crude material was used in the next reaction without further purification

Vorschrift

To a cold (-78° C.) solution of 2,2-dimethyl-4(tol-4-yl)-6-bromo-thiochrom-3-ene (Compound N, 280 mg, 0.81 mmol) in THF (5 mL) was added n-BuLi in hexane (1.6M solution, 0.66 mL). The mixture was gradually warmed to -10° C. over 25 min. and recooled to -78° C. To this solution was added DMF (80 mg, 1.1 mmol) and stirred at ambient temperature for 5 hours. The reaction was quenched by adding water (10 mL), ethyl acetate (100 mL), and the organic layer was washed with brine (10 mL), dried and the solvent removed by distillation. The crude material was used in the next reaction without further purification.

Quelle