反応 #2028303

反応方程式

potassium tert-butoxide

methyl 3-hydroxy-5-methoxy-1-methyl-1H-indole-2-carboxylate

water

chloroacetonitrile

→

product

収率 60.0%

Methyl 3-(cyanomethoxy)-5-methoxy-1-methyl-1H-indol-2-carboxylate

収率 60.0%

溶媒

dimethyl sulfoxide

反応条件

後処理

1. 1
   温度The mixture is heated at 80° for 90 minutes
2. 2
   温度cooled
3. 3
   ろ過The precipitated solid is filtered
4. 4
   洗浄washed with 10% methanol-water
5. 5
   その他recrystallized from aqueous acetonitrile

実験手順

A suspension of potassium tert-butoxide (3.2 g, 29 mmol) in 60 mL of dimethyl sulfoxide is treated in portions with methyl 3-hydroxy-5-methoxy-1-methyl-1H-indole-2-carboxylate (5.6 g, 24 mmol; Unangst P. C., et al., J. Heterocyclic Chem., 24:811 (1987)). The mixture is stirred for 15 minutes, and chloroacetonitrile (4.8 mL, 5.7 g, 76 mmol) is added dropwise. The mixture is heated at 80° for 90 minutes, cooled, and added to 800 g of ice and water. The precipitated solid is filtered, washed with 10% methanol-water, and recrystallized from aqueous acetonitrile to give 3.9 g (60%) of product, mp 136°-137° C.

出典