Lithium Hydroxide → (R)-2-(4-Cyano-3-fluoro-phenoxy)-propionic acid

HRID 350978Notes

Reaction equation

HRID 350978 reaction equation
C[O:2][C:3](=[O:16])[C@H:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[CH:8]=1)[CH3:5].[OH-].[Li+]>O1CCCC1.CO>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][C@H:4]([CH3:5])[C:3]([OH:16])=[O:2])=[CH:8][C:9]=1[F:15])#[N:14]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 60128060(R)-2-(4-Cyano-3-fluoro-phenoxy)-propionic Acid Methyl Ester

Product 1

HCID 60128038(R)-2-(4-Cyano-3-fluoro-phenoxy)-propionic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of (R)-2-(4-cyano-3-fluoro-phenoxy)-propionic acid methyl ester (0.40 g, 1.8 mmol) in 50 mL 1:1 tetrahydrofuran/methanol at room temperature was added lithium hydroxide (5.5 mL 1 M aqueous solution, 5.5 mmol) and the solution was stirred over night. The reaction was quenched into dilute aqueous hydrochloric acid and extracted with ethyl acetate. The organic layers were pooled and washed with brine, dried (Na2SO4) and concentrated in vacuo to afford a colorless oil (0.37 g, 98%).

Workup

  1. customThe reaction was quenched into dilute aqueous hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-060fa99416fc42a38af39679594e051c
Source dataset
uspto-grants-2007_02
Patent number
US07183293B2

Reaction notes

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