Lithium Hydroxide → HCID 59226463, compound

HRID 2192653Notes

Reaction equation

HRID 2192653 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH3:10])=[CH:4][C:3]=1[C:11]1[N:16]=[C:15]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:13][CH:12]=1.[OH-].[Li+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH3:10])=[CH:4][C:3]=1[C:11]1[N:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59226570HCID 59226570, compound

Product 1

HCID 59226463HCID 59226463, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(2-fluoro-5-propylphenyl)picolinate (1.0 equiv.) in THF was added lithium hydroxide (10 equiv.) and the reaction was stirred at room temperature for 1 hour. The THF solvent was removed in vacuo and the remaining basic phase was acidified with concentrated HCl. The aqueous layer was extracted with ethyl acetate (2×), the organic phase was dried with sodium sulfate, filtered and concentrated to give 6-(2-fluoro-5-propylphenyl)picolinic acid in 35% yield. LC/MS=260.2 (M+H), Rt=0.36 min.

Workup

  1. customThe THF solvent was removed in vacuo
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  3. dry with materialthe organic phase was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a879fc6d8b3b419ead108f49363ed2ac
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

Loading…