Water → (5-Methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanol

HRID 332485Notes

Reaction equation

HRID 332485 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:11][C:10]1[O:9][N:8]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:6]=1[CH2:4][OH:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22309063HCID 22309063, compound

Product 1

HCID 66643722(5-Methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanolYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methyl-3-pyridin-2-yl-isoxazole-4-carboxylic acid ethyl ester (4.1 g, 18 mmol) in THF (229 mL) at 0° C. was added lithium aluminum hydride (367 mg, 10 mmol). And the resulting mixture stirred for 1 h at room temperature. Water (1.9 mL) was added carefully followed by aqueous sodium hydroxide (15%, 1.9 mL) and water (0.54 mL). The resulting suspension was stirred for 15 min at ambient temperature and filtered over Hyflo®. Concentration and trituration with heptane afforded the title compound (2.88 g, 86%) as a light yellow solid. MS: m/e=191.3 [M+H]+.

Workup

  1. stirringThe resulting suspension was stirred for 15 min at ambient temperature
  2. filtrationfiltered over Hyflo®
  3. concentrationConcentration and trituration with heptane

Sources & evidence

ORD record
ord-2f8e61a654244fe4b37a13008f6913ff
Source dataset
uspto-grants-2014_11
Patent number
US08877783B2

Reaction notes

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