Hydrochloric Acid → HCID 22221339, compound

HRID 1794300Notes

Reaction equation

HRID 1794300 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14](OCC)=[O:15])[CH:5]=[CH:6][C:7]=1[F:8].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][OH:15])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221334HCID 22221334, compound

Product 1

HCID 22221339HCID 22221339, compoundYield 119.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(3,4-difluorophenyl)isoxazole-4-carboxylate (6.68 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (1.0 M tetrahydrofuran solution, 75 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-(3,4-difluorophenyl)-4-isoxazolylmethanol (6.68 g, yield 92%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 72–73° 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-cee3c3c816bb4b62a4e8db1acf34f718
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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