Aluminium lithium hydride → [5-(3-Chlorophenyl)isoxazol-3-yl]methanol

HRID 2102305Notes

Reaction equation

HRID 2102305 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[O:14][N:13]=1)=O)C>C1COCC1>[Cl:23][C:19]1[CH:18]=[C:17]([C:15]2[O:14][N:13]=[C:12]([CH2:10][OH:9])[CH:16]=2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 46929188Ethyl 5-(3-chlorophenyl)isoxazole-3-carboxylate

Product 1

HCID 57528605[5-(3-Chlorophenyl)isoxazol-3-yl]methanolYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (320 mg, 8.4 mmol) was slowly added to a solution of 5-(3-chloro-phenyl)-isoxazole-3-carboxylic acid ethyl ester (2.0 g, 8.4) in THF (100 mL) at room temperature. After 1 hour, the reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was then purified by flash column chromatography using 15-40% ethyl acetate in hexane to afford [5-(3-chloro-phenyl)-isoxazol-3-yl]-methanol (1.32 g, 75%, yellow solid). 1H NMR (CDCl3) δ (ppm): 7.78 (s, 1H), 7.68 (m, 1H), 7.43 (m, 2H), 6.63 (s, 1H), 4.84 (d, 2H), 2.23 (t, 1H).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was then purified by flash column chromatography

Sources & evidence

ORD record
ord-9312ac558b8a45419e0a622cc478468c
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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