Ethanol → 4-(cyclopropylmethoxy)-1H-indole-2-carboxylic acid

HRID 2267732Notes

Reaction equation

HRID 2267732 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][CH:17]1[CH2:20][CH2:19]C1)[CH:11]=[CH:10][CH:9]=2)=[O:5])C.[OH-].[K+].CCO>>[CH:17]1([CH2:16][O:15][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[CH:14]=[C:6]([C:4]([OH:3])=[O:5])[NH:7]3)[CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 668417824-cyclobutylmethoxy-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 668414344-(cyclopropylmethoxy)-1H-indole-2-carboxylic acid

Procedure

The 4-cyclobutylmethoxy-1H-indole-2-carboxylic acid ethyl ester 78 obtained above is mixed with a 2M-solution of KOH in EtOH (16.9 ml, 33.8 mmol) and stirred for 24 hours. The solvent is then evaporated and the residue is partitioned between water and DCM. The water layer is acidified with HCl and extracted twice with EtOAc. The combined organic layers are washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to give a white powder.

Workup

  1. customThe solvent is then evaporated
  2. customthe residue is partitioned between water and DCM
  3. extractionextracted twice with EtOAc
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a white powder

Sources & evidence

ORD record
ord-05dd1d74afd1460fb7e0d9e67398dad3
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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