Hydrochloric Acid → 3-[5-(4-Trifluoromethylphenyl)-4-isoxazolyl]propan-1-ol

HRID 1794396Notes

Reaction equation

HRID 1794396 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][CH2:15][C:16](OC)=[O:17])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][CH2:15][CH2:16][OH:17])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221371Methyl 3-[5-(4-trifluoromethylphenyl)-4-isoxazolyl]propionate

Product 1

HCID 222209803-[5-(4-Trifluoromethylphenyl)-4-isoxazolyl]propan-1-olYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[5-(4-trifluoromethylphenyl)-4-isoxazolyl]propionate (1.40 g) in tetrahydrofuran (80 ml) was gently added diisobutylaluminum hydride (1.0 M hexane solution, 10.3 ml) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into 2N hydrochloric acid, concentrated and the precipitated crystals were collected by filtration and recrystallized from ethyl acetate-hexane to give 3-[5-(4-trifluoromethylphenyl)-4-isoxazolyl]propan-1-ol (970 mg, yield 76%) as a colorless needle. melting point: 85–86° C.

Workup

  1. customat 0° C.
  2. concentrationconcentrated
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-df9b56ce085348c4a0c1de751d954195
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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