Reacción #591791

Ecuación de reacción

Water

ethyl 7-nitro-1H-indole-2-carboxylate

sodium hydride

Chloromethyl methyl ether

→

title compound

Rendimiento 77.0%

ethyl 1-(methoxymethyl)-7-nitro-1H-indole-2-carboxylate

Rendimiento 77.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 0° C.
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hr
3. 3
   Extracciónthe mixture was extracted with ethyl acetate
4. 4
   LavadoThe ethyl acetate layer was washed with saturated brine
5. 5
   Secadodried (MgSO4)
6. 6
   Concentraciónconcentrated

Procedimiento

To a suspension of sodium hydride (60%, in oil, 0.51 g) in N,N-dimethylformamide (15 ml) was slowly added ethyl 7-nitro-1H-indole-2-carboxylate (2.50 g) at 0° C., and the mixture was stirred for 30 min. Chloromethyl methyl ether (1.00 ml) was added to the reaction mixture over 20 min at 0° C., and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (2.29 g, yield 77%) as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). melting point 62-63° C.

Fuente