Aluminium lithium hydride → HCID 66643639, compound

HRID 1807487Notes

Reaction equation

HRID 1807487 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH2:12][CH2:13][CH3:14])=[N:8][O:9][C:10]=1[CH3:11])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:11][C:10]1[O:9][N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[C:6]=1[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66643541HCID 66643541, compound

Product 1

HCID 66643639HCID 66643639, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-methyl-3-propyl-isoxazole-4-carboxylic acid ethyl ester (13.8 g, 70 mmol) in THF (140 mL) under argon and at 0° C. was added lithium aluminium hydride (3.05 g, 80 mmol) in five portions. After 90 min the reaction mixture was quenched dropwise with Seignette salt solution. The reaction mixture was filtered and the filtrate extracted with ethyl acetate. The combined organic extracts were washed with Seignette salt solution then dried over sodium sulfate, filtered, concentrated and purified by chromatography (silica, 0 to 60% ethyl acetate in heptane) to give the title compound (8.7 g, 80%) as a yellow liquid. MS: m/e=232.2 [M+H]+.

Workup

  1. customAfter 90 min the reaction mixture was quenched dropwise with Seignette salt solution
  2. filtrationThe reaction mixture was filtered
  3. extractionthe filtrate extracted with ethyl acetate
  4. washThe combined organic extracts were washed with Seignette salt solution
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by chromatography (silica, 0 to 60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6fd7c12a91e44fe0afab23d6aefb3801
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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