Hydrochloric Acid → 5-(4-Trifluoromethylphenyl)-4-isoxazolylmethanol

HRID 1794326Notes

Reaction equation

HRID 1794326 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14](OCC)=[O:15])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][OH:15])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221374Ethyl 5-(4-trifluoromethylphenyl)isoxazole-4-carboxylate

Product 1

HCID 222214255-(4-Trifluoromethylphenyl)-4-isoxazolylmethanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(4-trifluoromethylphenyl)isoxazole-4-carboxylate (7.63 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (1.0 M hexane solution, 59 ml) at 0° C. and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give 5-(4-trifluoromethylphenyl)-4-isoxazolylmethanol (6.29 g, yield 97%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane to give a colorless prism. melting point: 106–107° C.

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cdcc21efe7934eb49cfb056072976335
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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