反応 #1938537

反応方程式

Water

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

sodium hydride

chloromethyl methyl ether

→

title compound

収率 77.0%

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

収率 77.0%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   その他at 0° C.
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hr
3. 3
   抽出the mixture was extracted with ethyl acetate
4. 4
   洗浄The ethyl acetate layer was washed with saturated brine
5. 5
   乾燥dried (MgSO4)
6. 6
   濃縮concentrated

実験手順

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. To the reaction mixture was added chloromethyl methyl ether (1.00 mL) at 0° C. over 20 min, 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 and the title compound (2.29 g, yield 77%) was obtained as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). melting point 62-63° C.

出典