Lithium Hydroxide → Methyl 4-iodopicolinate

HRID 901476Notes

Reaction equation

HRID 901476 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=1.[Li+].[OH-].O1CCOC[CH2:14]1.O>>[CH3:14][O:9][C:8](=[O:10])[C:4]1[CH:3]=[C:2]([I:1])[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 8182784-Iodopyridine-2-carboxylic acidHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 22742038Methyl 4-iodopicolinate

Procedure

To a solution of ester 11a′ (Z=ethyl, n=1; 25 mg, 0.07 mmol) in dioxane/water (3:1, 3 mL), LiOH (15.0 mg, 0.35 mmol) solid was added. The resulting mixture was stirred vigorously at rt for 3 h. The organic solvent was removed under reduced pressure, and the residue was dissolved in H2O (10 mL), acidified with aq. HCl (1.0 M) to pH value 3-4, and then extracted with DCM (3×15 mL). The combined organic layers were dried over MgSO4, the solvent was removed, and the residue was dried in high vacuum to afford the desired acid 11b′ (R=OEt, n=1; 22 mg, 95%) as colorless oil.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in H2O (10 mL)
  3. extractionextracted with DCM (3×15 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customthe solvent was removed
  6. customthe residue was dried in high vacuum

Sources & evidence

ORD record
ord-a7acee899357470293211711fbb3f5f4
Source dataset
uspto-grants-2008_04
Patent number
US07361743B2

Reaction notes

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