Reacción #337381

Ecuación de reacción

DMF

Oxalyl chloride

4-Methoxyindole

→

4-methoxy-1H-indole-3-carbaldehyde

Rendimiento 96.3%

Disolventes

dichloroethane

dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGThe solution was stirred until
3. 3
   Otrono more bubbling
4. 4
   workup.STIRRINGthe reaction mixture was stirred at room temperature for four hours
5. 5
   OtroThe reaction was quenched by careful addition of 10% sodium carbonate solution
6. 6
   workup.STIRRINGThe two phase mixture was stirred at room temperature for 2 hours
7. 7
   OtroThe layers were separated
8. 8
   Extracciónthe aqueous layer was extracted with methylene chloride
9. 9
   Otrothe combined organic extracts were dried
10. 10
    Otroevaporated to dryness
11. 11
    Lavadoeluting with 3:7 ethyl acetate

Procedimiento

A solution of dry DMF (0.75 g) in 50 ml dichloroethane was cooled to 0° C. and placed under nitrogen. Oxalyl chloride (1.03 g) dissolved in dichloroethane (5 ml) was added dropwise with stirring. The solution was stirred until no more bubbling was observed (about 15-20 m). 4-Methoxyindole (1.0 g, 6.7 mmole) was added to the solution as a solid and the reaction mixture was stirred at room temperature for four hours. The reaction was quenched by careful addition of 10% sodium carbonate solution. The two phase mixture was stirred at room temperature for 2 hours. The layers were separated and the aqueous layer was extracted with methylene chloride, and the combined organic extracts were dried and evaporated to dryness. The crude residue was passed through a short silica gel column, eluting with 3:7 ethyl acetate:hexane to 1:1 ethyl acetate:hexane to yield 1.13 g (95%) of 4-methoxy-1H-indole-3-carbaldehyde.

Fuente