Ethanol → HCID 18455625, compound

HRID 2221447Notes

Reaction equation

HRID 2221447 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:15]([O:17]CC)=[O:16])=[CH:9]2.O[Li].O.C(O)C>C1COCC1.O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:15]([OH:17])=[O:16])=[CH:9]2

Participants

6

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 23456828HCID 23456828, compound

Product 1

HCID 18455625HCID 18455625, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(2-methoxyethoxy)-1H-indole-2-carboxylate (2.0 g, 7.4 mmol) in THF (20 ml) was treated with a solution of LiOH•H2O (0.62 g, 14.8 mmol) in water (10 ml). Ethanol was added until a homogenous solution formed and stirring was continued for 16 h. The reaction mixture was diluted with water (50 ml) and the organic solvents were removed in vacuo. The pH was adjusted to 4 with 1M aqueous HCl and the aqueous solution was extracted with dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated in vacuo to provide 5-(2-methoxyethoxy)-1H-indole-2-carboxylic acid (1.7 g, 7.2 mmol) as a white solid. The crude acid was directly used without further purification.

Workup

  1. customformed
  2. customthe organic solvents were removed in vacuo
  3. extractionthe aqueous solution was extracted with dichloromethane
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b797644c0684f158253827aaf876b8d
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

Loading…