Hydrochloric Acid → 5-(But-2-ynyloxy)picolinic acid

HRID 1965040Notes

Reaction equation

HRID 1965040 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([O:14]C)=[O:13])=[N:10][CH:11]=1)[C:2]#[C:3][CH3:4].[OH-].[Li+].CCOC(C)=O.Cl>C1COCC1.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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 58449213Methyl 5-(but-2-yn-1-yloxy)picolinate2×

Product 1

HCID 679795075-(But-2-ynyloxy)picolinic acidYield 45.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(but-2-ynyloxy)picolinate (Intermediate 18, 1.42 g, 6.92 mmol) in THF (15 mL) was added lithium hydroxide (0.871 g, 20.76 mmol) dissolved in water (5 mL) to the reaction mixture at r.t. After 3 days of stirring was the reaction mixture partioned between water and EtOAc. The water was made acidic with aq. solution of HCl (2M) and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated to give 0.60 g (45% yield) of the title compound: 1H NMR (500 MHz, CD3OD) δ ppm 1.84 (t, 3 H), 4.87 (q, 2 H), 7.57 (dd, 1H), 8.14 (d, 1 H), 8.34 (d, 1 H); MS (ES+) m/z 192 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9d3e059dd23642319c8a62e040cb11fd
Source dataset
uspto-grants-2013_04
Patent number
US08415483B2

Reaction notes

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