تفاعل #84207

معادلة التفاعل

1-bromopentane

Indole 3-carboxylic acid

sodium hydride

→

title compound

المردود 49.0%

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

المردود 49.0%

المذيبات

DMF

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر