反応 #564019

反応方程式

DMF

Phosphorus oxychloride

DMF

1-methylindoline

→

5-formyl-1-methylindoline

収率 62.0%

溶媒

water

反応条件

後処理

1. 1
   workup.WAITat room temperature for 1 hour
2. 2
   workup.WAITfinally at 80° C. for 2 hours
3. 3
   workup.STIRRINGwith stirring
4. 4
   抽出extracted with ethyl ether
5. 5
   その他The crude oil was chromatographed on silica gel with 80/20 (v/v) CH2Cl2 /EtOAc
6. 6
   その他to yield 0.745 g

実験手順

Phosphorus oxychloride (1.23 g., 0.0080 mole) was slowly added dropwise to 5 ml. of DMF which was cooled in an ice bath. The solution was stirred for 5 minutes and to it there was added dropwise a solution of 1-methylindoline (1.0 g., 0.0075 mole) in 2 ml. of DMF. The resulting mixture was stirred in the ice bath for 5 minutes, then at room temperature for 1 hour and finally at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, slowly poured into water with stirring and extracted with ethyl ether. The crude oil was chromatographed on silica gel with 80/20 (v/v) CH2Cl2 /EtOAc to yield 0.745 g. (62% yield) of 5-formyl-1-methylindoline as a yellow solid, m.p. 39°-41° C.

出典