Réaction #84207

Équation de réaction

1-bromopentane

Indole 3-carboxylic acid

sodium hydride

→

title compound

Rendement 49.0%

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

Rendement 49.0%

Solvants

DMF

DMF

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source