反応 #49877

反応方程式

5-Methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide

sodium hydride

chloromethyl methyl ether

→

5-methoxy-1-methoxymethyl-3-(1-methylethoxy)-1H-indole-2-carboxamide

収率 31.8%

溶媒

ethyl acetate

dimethylformamide

dimethylformamide

反応条件

後処理

1. 1
   洗浄washed with brine
2. 2
   乾燥The organic layer is dried over MgSO4
3. 3
   ろ過Filtration
4. 4
   濃縮followed by concentration in vacuo and subsequent chromatography
5. 5
   洗浄eluting with 1:1 ethyl acetate

実験手順

5-Methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide (106 mg, 0.43 mmol) in 4 mL of dimethylformamide is added to a suspension of sodium hydride (60% by weight) (30 mg, 0.75 mol) in 2 mL of dimethylformamide. After 1 hour chloromethyl methyl ether (60 μL, 0.79 mmol) is added, and the solution is stirred at room temperature overnight. The reaction mixture is diluted with ethyl acetate and washed with brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and subsequent chromatography eluting with 1:1 ethyl acetate:hexane gives 40 mg of 5-methoxy-1-methoxymethyl-3-(1-methylethoxy)-1H-indole-2-carboxamide. An analytical sample was obtained by recrystallization from ethyl acetate:hexane; mp 145°-147° C.

出典