Aluminium lithium hydride → (3-Butyl-5-methyl-isoxazol-4-yl)-methanol

HRID 1807493Notes

Reaction equation

HRID 1807493 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH2:12][CH2:13][CH2:14][CH3:15])=[N:8][O:9][C:10]=1[CH3:11])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:12]([C:7]1[C:6]([CH2:4][OH:3])=[C:10]([CH3:11])[O:9][N:8]=1)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 665992233-Butyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester

Product 1

HCID 66599297(3-Butyl-5-methyl-isoxazol-4-yl)-methanolYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-butyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester (9.8 g, 46.3 mmol) in THF (100 mL) under argon and at 0° C. was added lithium aluminium hydride (2.03 g, 53.4 mmol) in five portions. After 1 h 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, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 4:6) afforded the title compound (7.5 g, 95%) as a yellow liquid. MS: m/e=170.3 [M+H]+.

Workup

  1. customAfter 1 h 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. customthen dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica, heptane:ethyl acetate=100:0 to 4:6)

Sources & evidence

ORD record
ord-014545409e9c446c973ccd0c6b2eb2b8
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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