Hydrochloric Acid → HCID 22221488, compound

HRID 1794306Notes

Reaction equation

HRID 1794306 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[O:15][N:14]=[CH:13][C:12]=2[C:16](OCC)=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[O:15][N:14]=[CH:13][C:12]=2[CH2:16][OH:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221239HCID 22221239, compound

Product 1

HCID 22221488HCID 22221488, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(3,4-dimethoxyphenyl)isoxazole-4-carboxylate (8.40 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (1.0 M tetrahydrofuran solution, 65 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-(3,4-dimethoxyphenyl)-4-isoxazolylmethanol (6.85 g, yield 96%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 83–84° 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-ee652d528bdb4886aec7dffaacd7049b
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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