Potassium Carbonate → ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate

HRID 420139Notes

Reaction equation

HRID 420139 reaction equation
C([O:4][C:5]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[CH:19]1[CH2:21][CH2:20]1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CCO>[CH:19]1([N:9]2[C:10]3[C:6](=[C:5]([OH:4])[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=3)[CH:7]=[CH:8]2)[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57930960ethyl 4-acetoxy-1-cyclopropyl-1H-indole-6-carboxylate

Product 1

HCID 57930939ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylateYield 80.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 72.33 g of ethyl 4-acetoxy-1-cyclopropyl-1H-indole-6-carboxylate in 360 ml of EtOH placed in a 2 L flask was added 69.58 g of K2CO3 and the mixture was stirred at room temperature for 4 hrs. EtOH was evaporated and the concentrate was diluted with EtOAc. The mixture was washed with water and saturated brine, dried over Na2SO4, and concentrated. The residue was triturated with toluene and n-hexane to give 49.78 g of ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate as a pale tan solid.

Workup

  1. customEtOH was evaporated
  2. additionthe concentrate was diluted with EtOAc
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was triturated with toluene and n-hexane

Sources & evidence

ORD record
ord-ac52cfdb4e7c4fa6b92ac6363b0b006c
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

Loading…