Sodium Hydroxide → HCID 9903190, compound

HRID 1007510Notes

Reaction equation

HRID 1007510 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([Si](C(C)(C)C)(C)C)[CH:21]=[C:20]3[CH:33]([CH3:35])[CH3:34])=[C:11]([CH3:36])[CH:10]=1)(C)(C)C.[OH-].[Na+]>C(O)C>[CH:33]([C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([O:16][C:12]3[C:11]([CH3:36])=[CH:10][C:9]([O:8][CH2:7][C:6]([OH:37])=[O:5])=[CH:14][C:13]=3[CH3:15])[CH:18]=2)[NH:22][CH:21]=1)([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 60110691HCID 60110691, compound

Product 1

HCID 9903190HCID 9903190, compoundYield 114.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.24 g (0.46 mmol) of tert-butyl-[4-({1-[tert-butyl-(dimethyl)silyl]-3-isopropyl-1H-indol-5-yl}oxy)-3,5-dimethylphenoxy]acetate (Example XIII) is introduced dissolved in 5 ml of ethanol and 2.5 ml (2.50 mmol) of 1N sodium hydroxide solution are added. The batch is stirred at room temperature for 2.5 h. The solvent is evaporated in a rotary evaporator, the batch is diluted with 50 ml of water and the mixture is acidified with 1N hydrochloric acid solution. The aqueous phase is extracted twice with ethyl acetate, the combined organic phases are dried and the solvent is removed in vacuo. 0.186 g (87.3%) of {4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethyl-phenoxy}acetic acid is obtained

Workup

  1. customThe solvent is evaporated in a rotary evaporator
  2. additionthe batch is diluted with 50 ml of water
  3. extractionThe aqueous phase is extracted twice with ethyl acetate
  4. customthe combined organic phases are dried
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7c6a32a5b360470d9ea1818b15672a48
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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