Hydrochloric Acid → HCID 22221119, compound

HRID 1794328Notes

Reaction equation

HRID 1794328 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:13][N:12]=[CH:11][C:10]=1[C:14](OCC)=[O:15].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:13][N:12]=[CH:11][C:10]=1[CH2:14][OH:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22220955HCID 22220955, compound

Product 1

HCID 22221119HCID 22221119, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(2,4-difluorophenyl)isoxazole-4-carboxylate (3.85 g) in tetrahydrofuran (60 ml) was gently added diisobutylaluminum hydride (1.0 M hexane solution, 33 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. The residue was subjected to silica gel column chromatography, and 5-(2,4-difluorophenyl)-4-isoxazolylmethanol (2.70 g, yield 84%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane to give a colorless prism. melting point: 60–61° 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-ef4b3ea51f5a426e92f9592c068b91dd
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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