Water → [3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol

HRID 1920919Notes

Reaction equation

HRID 1920919 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[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>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:7]2[C:6]([CH2:4][OH:3])=[C:10]([CH3:11])[O:9][N:8]=2)=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66599060HCID 66599060, compound

Product 1

HCID 66599256[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanolYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (2.5 g, 10 mmol) in dry THF (34 mL), cooled to 0° C., was added lithiumaluminiumhydride (209 mg, 2.3 mmol) portionwise. After allowing to warm up to room temperature over 1 h, the mixture was cooled to 0° C. and water (0.2 mL) was added carefully followed by aqueous sodium hydroxide (15%, 0.2 mL) and water (0.6 mL). The resulting suspension was stirred for 4 h at ambient temperature and filtered over Hyflo®. The filtrate was then concentrated and purification by chromatography (silica, heptane:ethyl acetate=50:50 to 0:100) afforded the title compound (1.47 g, 71%) as a light yellow solid. MS: m/e=209.1 [M+H]+.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. filtrationfiltered over Hyflo®
  3. concentrationThe filtrate was then concentrated
  4. custompurification by chromatography (silica, heptane:ethyl acetate=50:50 to 0:100)

Sources & evidence

ORD record
ord-59a8cac794f347b383733f9ffbb7ebc4
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

Loading…