Lithium hydroxide, monohydrate → 5-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid

HRID 1962952Notes

Reaction equation

HRID 1962952 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[CH:8][N:7]=1)=[O:5])C.O.[OH-].[Li+]>C1COCC1.O>[CH3:19][C:18]1[O:17][N:16]=[C:15]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]=1[CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]([OH:5])=[O:3])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 666443955-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 666444135-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acidYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid ethyl ester (481 mg, 1.42 mmol) in THF (12 mL) was added a solution of lithium hydroxide monohydrate (418 mg, 9.8 mmol) in water (6 mL) and the resulting mixture stirred at room temperature overnight. The mixture was acidified with HCl (1 N, 10 mL) and evaporation afforded the title compound (335 mg, 70%) which was obtained as a light yellow solid. MS: m/e=309.0 [M−H]−.

Workup

  1. customThe mixture was acidified with HCl (1 N, 10 mL) and evaporation

Sources & evidence

ORD record
ord-dc29f1ee2c264f81b6518c1a8d5adf7b
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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