Water → (5-Methyl-3-trifluoromethylisoxazol-4-yl)-methanol

HRID 1292811Notes

Reaction equation

HRID 1292811 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:13]([C:18]([F:21])([F:20])[F:19])=[N:14][O:15][C:16]=1[CH3:17])=O)C.C(OCC)(=O)C.O>C1COCC1>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]([F:21])([F:20])[F:19])[C:12]=1[CH2:10][OH:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 136639574-Ethoxycarbonyl-5-methyl-3-trifluoromethylisoxazoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 17862894(5-Methyl-3-trifluoromethylisoxazol-4-yl)-methanolYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0. 16 g (4.2 mmoles) of lithium aluminum hydride dissolved in 15 ml of THF was cooled to 0° C. Thereto was gradually added a solution of 0.93 g (4.2 mmoles) of 4-ethoxycarbonyl-5-methyl-3-trifluoromethylisoxazole dissolved in 15 ml of THF. The mixture was stirred at 0° C. for 1 hour to give rise to a reaction. After the completion of the reaction, ethyl acetate was added, followed by stirring for a while. Water was added, followed by stirring for a while. The reaction mixture was filtered under vacuum. The filtrate was extracted with diethyl ether. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 0.5 g (yield: 60.0%) of (5-methyl-3-trifluoromethylisoxazol-4-yl)-methanol.

Workup

  1. customto give rise
  2. customto a reaction
  3. additionwas added
  4. stirringby stirring for a while
  5. stirringby stirring for a while
  6. filtrationThe reaction mixture was filtered under vacuum
  7. extractionThe filtrate was extracted with diethyl ether
  8. washThe resulting organic layer was washed with an aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe resulting solution was subjected to vacuum distillation
  11. customto remove the solvent

Sources & evidence

ORD record
ord-a67832b2f6e44778a09f745c9833ca02
Source dataset
uspto-grants-2007_07
Patent number
US07238689B2

Reaction notes

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