Water → HCID 66643720, compound

HRID 1695423Notes

Reaction equation

HRID 1695423 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]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]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:6]=1[CH2:4][OH:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66643549HCID 66643549, compound

Product 1

HCID 66643720HCID 66643720, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methyl-3-(tetrahydro-pyran-4-yl)-isoxazole-4-carboxylic acid ethyl ester (4.0 g, 16.7 mmol) in THF (55 mL) at 0° C. was added lithium aluminum hydride (349 mg, 9.0 mmol). And the resulting mixture stirred for 18 h at room temperature. Water (0.5 mL) was added carefully followed by aqueous sodium hydroxide (15%, 1.0 mL) and water (2.2 mL). The resulting suspension was stirred for 15 min at ambient temperature and filtered over Hyflo®. The filtrate was then evaporated and purification by chromatography (silica, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (1.1 g, 34%) as a colorless gum.

Workup

  1. stirringThe resulting suspension was stirred for 15 min at ambient temperature
  2. filtrationfiltered over Hyflo®
  3. customThe filtrate was then evaporated
  4. custompurification by chromatography (silica, heptane:ethyl acetate=100:0 to 1:1)

Sources & evidence

ORD record
ord-0c87b6b354fb405c9ec37ba5e6a981d8
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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