Sodium Hydroxide → 3-[1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl]-4,4,4-trifluorobutanoic acid

HRID 1451528Notes

Reaction equation

HRID 1451528 reaction equation
[Br:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH:18]([C:25]([F:28])([F:27])[F:26])[CH2:19][C:20]([O:22]CC)=[O:21])=[C:8]2[CH3:29])=[CH:4][CH:3]=1.[OH-].[Na+].CCOCC.CCCCCC>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH:18]([C:25]([F:28])([F:26])[F:27])[CH2:19][C:20]([OH:22])=[O:21])=[C:8]2[CH3:29])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 19974932Ethyl 3-[1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl]-4,4,4-trifluorobutanoatHCID 21584099Diethylether hexane

Product 1

HCID 221489393-[1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl]-4,4,4-trifluorobutanoic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of the ester from Step 4 (4.6 g, 9.2 mmol) in 45 mL of EtOH was added 10N NaOH (2.3 mL, 23 mmol) and the mixture was heated to reflux for 2 h. The mixture was cooled and concentrated and the residue was partitioned between ether and 1M HCl. The organic layer was dried over MgSO4 and evaporated to give a white solid. This material was swished with 10% ether/hexane to give 4.0 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. customthe residue was partitioned between ether and 1M HCl
  6. dry with materialThe organic layer was dried over MgSO4
  7. customevaporated
  8. customto give a white solid

Sources & evidence

ORD record
ord-50847f5d1f97465fabf729316bda380b
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

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