Water → 1-(2-Acetoxyethyl)indole

HRID 345695Notes

Reaction equation

HRID 345695 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.N1C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20].O>C(OCC)C>[C:19]([O:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 137349961H-Indole-1-ethanol

Product 1

HCID 151630421-(2-Acetoxyethyl)indole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An ice-cooled solution of 4.6 g of 1-(2-hydroxyethyl)indole in 10 ml of diethyl ether was treated with 1 ml of pyridine and 4 ml of acetic anhydride. After 2 hours 50 ml of water were added, the mixture was extracted with 100 ml of dichloromethane and the dichloromethane extract was dried. The solvent was evaporated to give 5.7 g of 1-(2-acetoxyethyl)indole.

Workup

  1. extractionthe mixture was extracted with 100 ml of dichloromethane
  2. extractionthe dichloromethane extract
  3. customwas dried
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-74e2b27d5c1b475ab3a08e261f416d25
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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