Lithium Hydroxide → 5-(But-2-ynyloxy)picolinic acid

HRID 627727Notes

Reaction equation

HRID 627727 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([O-:14])=[O:13])=[N:10][CH:11]=1)[C:2]#[C:3][CH3:4].[OH-].[Li+]>CO.O1CCOCC1.O>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 867281605-(But-2-yn-1-yloxy)picolinate

Product 1

HCID 679795075-(But-2-ynyloxy)picolinic acidYield 83.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-(but-2-yn-1-yloxy)picolinate (72 mg, 0.35 mmol) in methanol (1 ml), dioxane (1 ml) and water (0.1 ml) was added lithium hydroxide (31 mg, 1.3 mmol). The reactions were stirred at ambient temperature for 2 h. The solvents were removed in vacuo. The residue from the reaction was triturated with 0.5 mL 1 N aqueous HCl. The tan precipitate was collected by vacuum filtration, washed with water, and dried in vacuo to generate 5-(but-2-yn-1-yloxy)picolinic acid (56 mg, 0.293 mmol, 83% yield) as a tan powder. LC/MS (ESI+) m/z=192 (M+H).

Workup

  1. customThe solvents were removed in vacuo
  2. customThe residue from the reaction was triturated with 0.5 mL 1 N aqueous HCl
  3. filtrationThe tan precipitate was collected by vacuum filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bcd9446daf514f959cb0506703fd5fa0
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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