Lithium Hydroxide → 4-Pentynoic acid, 5-[3-(trifluoromethoxy)phenyl]-

HRID 751204Notes

Reaction equation

HRID 751204 reaction equation
C([O:8][C:9](=[O:25])[CH2:10][CH2:11][C:12]#[C:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=1)C1C=CC=CC=1.[Li+].[OH-]>C1COCC1.CO>[F:22][C:21]([F:23])([F:24])[O:20][C:16]1[CH:15]=[C:14]([C:13]#[C:12][CH2:11][CH2:10][C:9]([OH:25])=[O:8])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 688239995-(3-Trifluoromethoxy-phenyl)-pent-4-ynoic acid benzyl ester

Product 1

HCID 688226644-Pentynoic acid, 5-[3-(trifluoromethoxy)phenyl]-Yield 100%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 5-(3-trifluoromethoxy-phenyl)-pent-4-ynoic acid benzyl ester (500 mg, 1.4 mmol) in THF/methanol 2/1 (13.5 ml) was added 1 N aqueous LiOH solution (8.6 ml). The reaction mixture was stirred for 2 h at ambient temperature and concentrated under reduced pressure. The residue was dissolved in 1 N NaOH/ice water 1/1 and ethyl acetate and the layers were separated. The aqueous layer was brought to pH 1 with 1 N HCl and extracted two times with ethyl acetate. The combined extracts were washed with ice water/brine 1/1, dried over sodium sulfate and the solvent was evaporated in vacuo to give the title compound (370 mg, 1.4 mmol, quant.) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 1 N NaOH/ice water 1/1
  3. customethyl acetate and the layers were separated
  4. extractionextracted two times with ethyl acetate
  5. washThe combined extracts were washed with ice water/brine 1/1
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-7fdb1d019ba1426daf1537e4c8c41ab3
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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