Ethanol → Ethyl 4-(1H-indol-1-yl)butanoate

HRID 1680478Notes

Reaction equation

HRID 1680478 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1)([OH:8])=[O:7].[CH2:21](O)[CH3:22]>>[CH2:21]([O:7][C:6]([CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1)=[O:8])[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 24813Phosphorus oxychlorideHCID 10241973HCID 10241973, compound

Product 1

HCID 19024819Ethyl 4-(1H-indol-1-yl)butanoate

Procedure

Phosphorus oxychloride (10 ml) was added dropwise with cooling to a stirred solution of 1-(3-carboxypropyl)indole (100 g) in ethanol (750 ml). The solution was heated under reflux for 8 hours and then evaporated. The residue was distilled to give 1-(3-ethoxycarbonylpropyl)indole (95.0 g), b.p. 164°-170° C./2 m.m.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 8 hours
  3. customevaporated
  4. distillationThe residue was distilled

Sources & evidence

ORD record
ord-acf9f6e179c246908b2c4ef391dbdf60
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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