Lithium Hydroxide → HCID 11699185, compound

HRID 1452692Notes

Reaction equation

HRID 1452692 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])[CH:16]=2)=[CH:7][CH:6]=1.[Li+].[OH-].OS([O-])(=O)=O.[K+]>C1COCC1>[C:31]1([CH:12]([O:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:37])=[O:2])=[CH:10][CH:9]=2)[CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])[CH:16]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 11598965HCID 11598965, compound

Product 1

HCID 11699185HCID 11699185, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

40 mg (0.08 mmol) of rac (4-{1-phenyl-2-[3-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-phenyl)-acetic acid methyl ester (example 9) in 1 mL of THF were treated with 0.76 mL of 1M LiOH at room temperature for 2 h. 1M KHSO4 solution was added, the phases were separated, and the inorganic one was extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated. The crude product was purified by column chromatography to give 29 mg (74%) of rac (4-{1-phenyl-2-[3-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-phenyl)-acetic acid as a colorless oil, MS: 513 (M−H)−.

Workup

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-2c9ea62981e7473b92718d6a67a12996
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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