Hydrochloric Acid → 5-(4-Nitrophenyl)-4-isoxazolylmethanol

HRID 1794302Notes

Reaction equation

HRID 1794302 reaction equation
[N+:1]([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)([O-:3])=[O:2].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:14][N:13]=[CH:12][C:11]=2[CH2:15][OH:16])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221151HCID 22221151, compound

Product 1

HCID 222210625-(4-Nitrophenyl)-4-isoxazolylmethanolYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(4-nitrophenyl)isoxazole-4-carboxylate (9.06 g) in tetrahydrofuran (50 ml) was gently added diisobutylaluminum hydride (1.0 M tetrahydrofuran solution, 80 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 5-(4-nitrophenyl)-4-isoxazolylmethanol (7.16 g, yield 94%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 170–171° 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-99922c37909642ebaf2896c5c0d9e681
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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