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

HRID 732119Notes

Reaction equation

HRID 732119 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 r.t After 1 h, the reaction mixture was quenched with water and then extracted with EA. The organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated. The resulting residue was then purified by column chromatography using 15-40% EA in hex. to afford the title compound (1.32 g, 75%,). 1H NMR: 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 EA
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was then purified by column chromatography

Sources & evidence

ORD record
ord-eb43f023bf204498996acd380a13cc79
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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