反応 #216747

反応方程式

hydrochloric acid

sodium hydride

3-indolecarboxylic acid

1-iodobutane

→

1-butylindole-3-carboxylic acid

収率 86.1%

溶媒

—

ice water

DMF

DMF

DMF

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred for 30 minutes
2. 2
   workup.STIRRINGThe mixture was stirred for approximately 12 hours
3. 3
   抽出extracted 3 times with ethyl acetate
4. 4
   洗浄washed twice with water
5. 5
   乾燥dried over magnesium sulfate
6. 6
   濃縮The mixture was concentrated
7. 7
   workup.ADDITIONthe residue mixed with diethylether
8. 8
   ろ過Filtration

実験手順

A suspension of sodium hydride (34.1 g, 1.42 mol) in 300 mL of DMF was stirred in an ice/methanol bath and a solution of 3-indolecarboxylic acid (55.0 g, 0,374 mol) in 250 mL DMF was added dropwise over 45 minutes. The mixture was stirred for 30 minutes and then 100 mL of additional DMF was added. The mixture was cooled to 0° C. and 1-iodobutane (8.79 g, 40.8 mL, 0.359 mol) was added. The mixture was stirred for approximately 12 hours. The mixture was then poured in 2.0 L of ice water, acidified with 1N hydrochloric acid, extracted 3 times with ethyl acetate, washed twice with water and then dried over magnesium sulfate. The mixture was concentrated and the residue mixed with diethylether. Filtration gave 1-butylindole-3-carboxylic acid (62.74 g, 0.309 mol) as a white powder.

出典