Hydrochloric Acid → HCID 22221405, compound

HRID 1794334Notes

Reaction equation

HRID 1794334 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13](OCC)=[O:14])=[CH:4][C:3]=1[CH3:18].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][OH:14])=[CH:4][C:3]=1[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221423HCID 22221423, compound

Product 1

HCID 22221405HCID 22221405, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(4-chloro-3-methylphenyl)isoxazole-4-carboxylate (8.50 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (1.5 M toluene solution, 47 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 to give 5-(4-chloro-3-methylphenyl)-4-isoxazolylmethanol (6.13 g, yield 86%) as colorless crystals, which were recrystallized from ethyl acetate-hexane to give a colorless needle. melting point: 92–93° 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-6989769f54394e8ea0c9066c374cf5fa
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

Loading…