Hydrochloric Acid → HCID 69561763, compound

HRID 1794425Notes

Reaction equation

HRID 1794425 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][CH2:15][C:16](OC)=[O:17])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][CH2:15][CH2:16][OH:17])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 17857671HCID 17857671, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 69561763HCID 69561763, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[5-(4-methylthiophenyl)-4-isoxazolyl]propionate (1.60 g) in tetrahydrofuran (60 ml) was gently added diisobutylaluminum hydride (0.95 M toluene solution, 15.2 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 the crystals obtained from a fraction eluted with acetone-hexane (1:1, volume ratio) were recrystallized from ethyl acetate-hexane to give 3-[5-(4-methylthiophenyl)-4-isoxazolyl]propan-1-ol as a colorless prism crystal (1.36 g, yield 95%). melting point: 54–55° 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
  6. customthe crystals obtained from a fraction
  7. washeluted with acetone-hexane (1:1, volume ratio)
  8. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-912503b00dfd48f4855b0ec141fd0963
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

Loading…