Water → HCID 67157972, compound

HRID 332371Notes

Reaction equation

HRID 332371 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=O)C.O.[OH-].[Na+]>C1COCC1>[CH3:11][C:10]1[O:9][N:8]=[C:7]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:6]=1[CH2:4][OH:3]

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 22137723Ethyl 5-methyl-3-pyridin-4-ylisoxazole-4-carboxylate

Product 1

HCID 67157972HCID 67157972, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methyl-3-pyridin-4-yl-isoxazole-4-carboxylic acid ethyl ester (7.06 g, 17.3 mmol) in THF (350 mL) was added at 5° C. lithiumaluminumhydride (635 mg, 16.7 mmol). After stirring for 2 h at this temperature further lithiumaluminumhydride (318 mg, 8.4 mmol) was added and stirred for 1 h at 5° C. Water (1.9 mL) was added carefully follwed by aqueous sodium hydroxide (15%,1.9 mL) and water (0.540 mL). The resulting suspension was stirred for 15 min at ambient temperature and filtered over Hyflo®. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=50:50 to 0:100) afforded the title compound (2.15 g, 65%) as a light yellow solid. MS: m/e=191.2 [M+H]+.

Workup

  1. additionwas added
  2. stirringstirred for 1 h at 5° C
  3. stirringThe resulting suspension was stirred for 15 min at ambient temperature
  4. filtrationfiltered over Hyflo®
  5. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=50:50 to 0:100)

Sources & evidence

ORD record
ord-ddc19cafb19947819478271de8a83a22
Source dataset
uspto-grants-2014_11
Patent number
US08877783B2

Reaction notes

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