Hydrochloric Acid → HCID 22220981, compound

HRID 1794296Notes

Reaction equation

HRID 1794296 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[CH:12][C:11]=2[C:15](OCC)=[O:16])=[CH:6][CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[F:21][C:2]([F:1])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[CH:12][C:11]=2[CH2:15][OH:16])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221244HCID 22221244, compound

Product 1

HCID 22220981HCID 22220981, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(4-trifluoromethoxyphenyl)isoxazole-4-carboxylate (6.60 g) in tetrahydrofuran (80 ml) was gently added diisobutylaluminum hydride (1.0 M tetrahydrofuran solution, 55 ml) at 0° C. 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 5-(4-trifluoromethoxyphenyl)-4-isoxazolylmethanol (5.70 g, yield 99%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 45–46° 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-19ebecd790c34dc385a5df7b5184e8ef
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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