Water → HCID 68153516, compound

HRID 1405376Notes

Reaction equation

HRID 1405376 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:12]([O-:14])=[O:13])=[N:9][C:10]=1[CH3:11])([CH3:3])[CH3:2].[Li+].[OH-].O.CCOC(C)=O>C1COCC1.O>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[N:9][C:10]=1[CH3:11])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 86668525HCID 86668525, compound

Product 1

HCID 68153516HCID 68153516, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

5-Isopropoxy-6-methylpicolinate (1.3 g, 6.22 mmol) was dissolved in THF/water 2:1 (9 mL). LiOH*H2O (0.26 g, 6.22 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was poured into a mixture of water and EtOAc and the layers were separated. The aqueous layer was acidified to pH 4 with 2 N HCl and was extracted with EtOAc (2×). The combined organics were dried (Na2SO4) and concentrated to give 5-isopropoxy-6-methylpicolinic acid (860 mg, 74%) as a beige solid. 1H-NMR (300 MHz, DMSO-d6) 1.31 (d, 6H), 4.73 (m, 1H), 7.44 (d, 1H), 7.86 (d, 1H). 1H NMR (400 MHz, DMSO) δ 12.61 (s, 1H), 7.88 (d, J=8.5 Hz, 1H), 7.44 (d, J=8.7 Hz, 1H), 4.74 (dt, J=12.0, 6.0 Hz, 1H), 2.37 (s, 3H), 1.32 (d, J=6.0 Hz, 6H).

Workup

  1. customthe layers were separated
  2. extractionwas extracted with EtOAc (2×)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-137f9c2ab9dc48a4ad649c13427191a6
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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