Hydrochloric Acid → HCID 22221163, compound

HRID 1794322Notes

Reaction equation

HRID 1794322 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14](OCC)=[O:15])=[CH:12][O:11][N:10]=2)=[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[C:13]([CH2:14][OH:15])=[CH:12][O:11][N:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221265Ethyl 3-[4-(trifluoromethyl)phenyl]-4-isoxazolecarboxylate

Product 1

HCID 22221163HCID 22221163, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(4-trifluoromethylphenyl)isoxazole-4-carboxylate (8.00 g) in tetrahydrofuran (150 ml) was gently added diisobutylaluminum hydride (1.0 M tetrahydrofuran solution, 60 ml) at 0° C. and the mixture was stirred at room temperature for 30 min. 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 3-(4-trifluoromethylphenyl)-4-isoxazolylmethanol (6.46 g, yield 95%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 70–71° 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-b6b11380bcb6433fb96da53ebbcabd16
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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