Hydrochloric Acid → HCID 22221372, compound

HRID 1794420Notes

Reaction equation

HRID 1794420 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[CH2:13][CH2:14][C:15](OC)=[O:16])=[CH:4][C:3]=1[CH3:19].[H-].C([Al+]CC(C)C)C(C)C.O.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][CH2:14][CH2:15][OH:16])=[CH:4][C:3]=1[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 22221444HCID 22221444, compound

Product 1

HCID 22221372HCID 22221372, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[5-(4-chloro-3-methylphenyl)-4-isoxazolyl]propionate (1.20 g) in tetrahydrofuran (40 ml) was gently added diisobutylaluminum hydride (1.0 M toluene solution, 9.5 ml) at 0° C., and the mixture was stirred at room temperature for 3 hr. Water was carefully added to the reaction mixture, acidified with dilute hydrochloric acid and 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 the crystals obtained from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio) were recrystallized from ethyl acetate-hexane to give a colorless needle of 3-[5-(4-chloro-3-methylphenyl)-4-isoxazolyl]propan-1-ol (780 mg, yield 72%). melting point: 50–51° C.

Workup

  1. customat 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customthe crystals obtained from a fraction
  7. washeluted with ethyl acetate-hexane (1:1, volume ratio)
  8. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d7118484cbbd4abda8d7fc1e3a8dbb32
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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