Aluminium lithium hydride → 2-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-ethanol

HRID 1512570Notes

Reaction equation

HRID 1512570 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:7]([CH3:18])=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOC(C)=O.Cl>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[O:9][N:8]=[C:7]([CH3:18])[C:6]=2[CH2:5][CH2:4][OH:3])=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66577263[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetic acid ethyl ester

Product 1

HCID 665772962-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-ethanol

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-acetic acid ethyl ester (1.37 mmol) in THF (3 mL) at 0° C. was added lithium aluminum hydride (0.060 g, 1.47 mmol). The reaction was stirred at room temperature for 1 hour. The mixture was diluted with EtOAc and 1 N aqueous HCl, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give the title compound.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1cdd49bad8fd4fd8a558193fdcdb94b6
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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