反応 #84207

反応方程式

1-bromopentane

Indole 3-carboxylic acid

sodium hydride

→

title compound

収率 49.0%

3-carboxy-1-pentyl-1H-indole

収率 49.0%

溶媒

DMF

DMF

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature overnight
2. 2
   その他The solvents were removed in vacuo and to the residue
3. 3
   workup.ADDITIONwas added water (30 ml) and ethyl acetate (30 ml)
4. 4
   その他The ethyl acetate portion was separated
5. 5
   乾燥dried over sodium sulphate
6. 6
   ろ過filtered
7. 7
   その他evaporated to dryness
8. 8
   その他The crude residue was purified by column chromatography (silica gel: 20% ethyl acetate in hexane)

実験手順

Indole 3-carboxylic acid (3 g, 18.62 mmol) was added to a suspension of sodium hydride (60% in oil) (1.11 g, 1.5 eq) in dry DMF (30 ml) under a nitrogen atmosphere. The mixture was stirred at room temperature for 45 min (H2 evolving has ceased) and to this was added 1-bromopentane (4.62 ml, 2 eq) in dry DMF (10 ml) dropwise. The mixture was stirred at room temperature overnight. The solvents were removed in vacuo and to the residue was added water (30 ml) and ethyl acetate (30 ml). The ethyl acetate portion was separated, dried over sodium sulphate, filtered and evaporated to dryness. The crude residue was purified by column chromatography (silica gel: 20% ethyl acetate in hexane) to give the title compound (2.12 g, 49%) as a cream solid.

出典