Lithium Hydroxide → HCID 11669619, compound

HRID 1452696Notes

Reaction equation

HRID 1452696 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[CH3:31])=[CH:6][CH:5]=1.[Li+].[OH-].OS([O-])(=O)=O.[K+]>C1COCC1>[CH3:31][C:16]1[CH:17]=[C:18]([C:21]([OH:30])([C:22]([F:25])([F:23])[F:24])[C:26]([F:27])([F:29])[F:28])[CH:19]=[CH:20][C:15]=1[O:14][CH2:13][CH2:12][CH2:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:32])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 11698407HCID 11698407, compound

Product 1

HCID 11669619HCID 11669619, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

94 mg (0.2 mmol) of 4-{3-[2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-propoxy}-benzoic acid methyl ester (example 19) in 2 mL of THF were treated with 2 mL of 1M LiOH at room temperature overnight. 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 with CH2Cl2/MeOH 95:5 to give 60 mg (65%) 4-{3-[2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-propoxy}-benzoic acid as a light yellow solid, MS: 451 (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 with CH2Cl2/MeOH 95:5

Sources & evidence

ORD record
ord-45463148579245d5b13e2cfe636b2713
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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